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Journal of Molecular Structure 1207 (2020) 127847
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The self-assembly of supramolecular helical chains in crystallized compounds of methionine with inorganic/organic acids Chunying Zheng a, *, Caiwei Liu b, Xinyang Zhang a a b
School of Environmental and Municipal Engineering, Qingdao University of Technology, Qingdao, 266033, PR China College of Civil Engineering, Qingdao University of Technology, Qingdao, 266033, PR China
a r t i c l e i n f o
a b s t r a c t
Article history: Received 25 December 2019 Received in revised form 29 January 2020 Accepted 3 February 2020 Available online 4 February 2020
In this paper, the supramolecular helical chains are found in eight crystallized compounds of methionine with inorganic/organic acids for the first time. The self-assembly and the components of supramolecular helical chains are analyzed in detail, and the supramolecular helical features are summarized in this contribution, which may throw light on the nature of biomolecular aggregation patterns and intermolecular interactions about methionine compounds. © 2020 Elsevier B.V. All rights reserved.
1. Introduction Weak interactions including van der Waals, p-p interactions and various hydrogen bonds play an important role in the crystal packing of compounds [1e8]. Amino acids usually exist in the form of zwitterions that contain protonated amino groups (-NHþ 3 ) and deprotonated carboxylic acid groups (-COO-), which induce amino acids to be natural building blocks for supramolecular H-bonding networks [9e14] and may introduce novel biological, physical and chemical properties [15,16]. Methionine is a straight-chain aliphatic-amino acid and is one of few sulfur-containing amino acids [17]. Methionine shows an important antioxidant because of its sulfur group, and is also very important as a donor of an active methyl group [18,19]. Methionine is buried within proteins, and contributes to the synthesis of many important substances, and is indispensable for normal maintenance, metabolism and growth of body tissues, and is involved in many very important processes, such as the transfer of methyl groups and sulfur metabolism and the initiation of translation of messenger RNA [20]. Previous reports about crystallized compounds of methionine with inorganic/organic acids (methionine -acid compounds) mainly focus on studying the conformation and hydrogen-bonding features of methionine in the presence of inorganic/organic acids, which are expected to provide useful information regarding biomolecular aggregation patterns [21e33]. Rare report is about the self-assembly of supramolecular helical chains in methionine-acid
compounds. The supramolecular helical chain is of prime importance for understanding of the origins of life, the potential chemical properties and the potential physical properties [34e38]. And, understanding the self-organizing way of supramolecular helical chain is still an essential question for chemists [39e42]. In this paper, we analyzed twelve compounds of methionine with inorganic/organic acids (methionine-acid compounds) from the Cambridge Crystallographic Data Centre database before 2020 in the aspect of the way of methionine self-organizing into supramolecular helical chains. The supramolecular helical chains were found in eight methionine-acid compounds for the first time. The supramolecular helical models and the possible influencing factors on the self-assembly of supramolecular helical chains in methionine-acid compounds were discussed and summarized in detail. 2. Results and discussion In this paper, according to the components of supramolecular helical chains in each compound, the supramolecular helical models in the eight methionine-acid compounds are classified into five types, named type 1, type 2, type 3, type 4 and type 5. And then, according to the number and the chirality of supramolecular helical chains in each compound, the supramolecular helical models are further classified into seven types, named type 1-1, type 1e2, type 2e1, type 2-2, type 3, type 4 and type 5. 2.1. The supramolecular helical model, type 1-1
* Corresponding author. E-mail address: [email protected] (C. Zheng). https://doi.org/10.1016/j.molstruc.2020.127847 0022-2860/© 2020 Elsevier B.V. All rights reserved.
The asymmetric unit of compound DL-methioni- nium nitrate
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C. Zheng et al. / Journal of Molecular Structure 1207 (2020) 127847
Fig. 1. a) The asymmetric unit of compound 1; b) The right-handed supramolecular helical chains (P-helix) in compound 1; c) The left-handed supramolecular helical chains (M-helix) in compound 1; d) The 3D packing picture in compound 1, viewed from b-axis.
(1) [22] contains a protonated DL-methionine molecule (DLmethioninium molecule) (CH3SCH2CH2CHNHþ 3 COOH) and a free nitrate ion (NO 3 ) (Fig. 1a). The carboxylate oxygen atom (O2) of a DL-methioninium molecule connects the oxygen atom (O2#1) from an adjacent DL-methioninium molecule by a type of hydrogen bond interaction (O2e H12/O2#1, 2.972 Å, O2eO2#1, 3.479 Å, O2e H12/O2#1, 119.10 ) (Table S1) to develop equivalent right handed (P-Helix) and left handed (M-Helix) supramolecular helical chains (Fig. 1b and c). The left handed supramolecular helical chains and the right handed ones are alternately packed by van der Waals to extent the 3D structure in compound 1 (Fig. 1d). The supramolecular helical model of compound 1 is named type 1-1. There is only a DL-methionine molecule in the asymmetric unit of compound 1. There are two kinds of supramolecular helical chains (the left-handed chain and the right-handed chain) in compound 1. And, the two supramolecular helical chains are composed only by the self-organizing of DL-methionine molecules, and the two supramolecular helical chains are enantiomer.
2.2. The supramolecular helical model, type 1-2 The asymmetric unit of compound L-methioninium nitrate (2) [23] contains two protonated L-meth- ionine molecules (L-methionine molecules) (pink and light blue bounds) (CH3SCH2CH2CHNHþ 3 COOH) and two free nitrate ions (NO3 ) (Fig. 2a). The carboxylate oxygen atom (O1) from a L-methionine molecule (pink bounds) is connected to the amino nitrogen (N1) from an adjacent one by a type of hydrogen bond interaction
Fig. 2. a) The asymmetric unit of compound 2; b) and c) The left-handed supramolecular helical chains (M-helix) in compound 2; d) The 2D sheet in compound 2; e) The 3D packing picture in compound 2, viewed from b-axis.
(N1eH5/O1 ¼ 2.083 Å, N1eO1, 2.858 Å, N1eH5/O1. 144.96 (Table S1) to develop equable left handed (M-Helix) supramolecular helical chains (Fig. 1b). Similarly, the carboxylate oxygen atom (O3) from a L-methionine molecule (light blue bounds) is connected to the amino nitrogen (N2) from an adjacent one by a type of hydrogen bond interaction (N2eH17/O3, 2.097 Å, N2eO3, 2.877 Å, N2eH17/O3, 144.14 ) (Table S1) to develop another left handed (M-Helix) supramolecular helical chains (Fig. 1c). The oxygen atom (O9) and oxygen atom (O10) from a nitrate ion with N4 atom connect a amino nitrogen atom (N2) from a L-methionine molecule (light blue bounds) and a carboxylate oxygen atom (O2) from a L-methionine molecule (pink bounds) by two types of hydrogen bond interactions (N2eH16/O9, 2.002 Å, N2eO9, 2.840 Å, N2eH16/O9, 156.51 and O2e H1/O10, 1.895 Å, O2eO10, 2.663 Å, O2eH1/O10, 168.69 ), respectively. Thus, the two kinds of left handed supramolecular helical chains are connected alternately to give rise to the 2D structure in compound 2 (Fig. 2d). The nitrate ion with N3 atom connect the amino nitrogen (N1) from a L-methionine molecule (pink bounds) by a type of hydrogen bond interaction (N1eH4/O7, 2.008 Å, N1eO7, 2.854 Å, N1eH4/O7, 158.45 ). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 2 (Fig. 2e). The supramolecular helical model of compound 2 is named type 1e2. There are two L-methionine molecules in the asymmetric unit of compound 2. There are also two kinds of supramolecular helical chains. And they are constructed only by the self-organizing of two L-methionine molecules, respectively, but they are not enantiomer. The comment features of type 1-1 and type 1e2 are that compounds 1 and 2 contain two kinds of the supramolecular helical chains and they are constructed only by the methionine molecules. 2.3. The supramolecular helical model, type 2-1 The asymmetric unit of compound L-methioninium chloride (3) [24] contains a protonated L-meth- ionine molecule (L-methioninium molecule) (CH3Se CH2CH2CHNHþ 3 COOH) and a free chloride ion (Cl) (Fig. 3a). The chloride ion (Cl1) acts as a m3-linker. First, the chloride ion (Cl1) connects the amino nitrogen (N1) and the amino nitrogen (N1#2) from two L-methioninium molecules through two
Fig. 3. a) The asymmetric unit of compound 3; b) The left-handed supramolecular helical chains (M-helix) in compound 3; c) The 2D sheet in compound 3; d) The 3D packing picture in compound 3, viewed from a-axis.
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Fig. 4. a) The asymmetric unit of compound 4; b) The left-handed supramolecular helical chains (M-helix) in compound 4; c) The 3D packing picture in compound 4, viewed from b-axis.
types of hydrogen bond interactions (N1eH12/Cl1, 2.512 Å, N1eCl1, 2.854 Å, N1eH12/Cl1, 158.45 and N1#2-H11$$$Cl1, 2.396 Å, N1#2-Cl1, 2.838 Å, N1#2-H11$$$Cl1, 179.450 ) (Table S1) to develop the equable left-handed (M-Helix) supramolecular helical chains (Fig. 3b). Second, the chloride ion (Cl1) connects the amino nitrogen (N1#3) from another. L-methioninium molecule through a type of hydrogen bond interaction (N1#3-H10$$$Cl1, 2.364 Å, N1#3-Cl1, 3.184 Å, N1#3H10$$$Cl1, 174.74 ) (Table S1) to develop the 2D sheets in compound 3 (Fig. 3c). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 3 (Fig. 3d). The asymmetric unit of compound D-methionine (þ)-18-crown6 tetracarboxylic acid ((þ)-18C6H4) (4) [25] contains a protonated D-methionine molecule (D-methioninium molecule) (CH3SCH2CH2CHNHþ 3 - COOH), a (þ)-18C6H4 molecule and three water molecules (Fig. 4a). The carboxylate oxygen atom (O18) and the amino nitrogen (N1) from a D-methioninium molecule connect the carboxylate oxygen atom (O17) and the carboxylate oxygen atom (O10) from two adjacent (þ)-18C6H4 molecules by two types of hydrogen bond interactions (O18eH28/O17, 1.546 Å, O18eO17, 2.555 Å, O18e H28/O17,155.40 and N1eH24/O10, 2.063 Å, N1e O10, 3.000 Å, N1eH24/O10, 168.24 ) (Table S1) to develop equivalent left handed (M-Helix) supramolecular helical chains (Fig. 4b). The left handed supramolecular helical chains are parallelly packed by van der Waals to extent the 3D structure in compound 4 (Fig. 4c). The supramolecular helical model of compounds 3 and 4 is named type 2e1. There is a methionine molecule in the asymmetric unit of compounds 3 and 4. There is only a kind of supramolecular helical chain in compound 3 and compound 4, which is constructed by part of protonated L-methionine molecules and free chloride ions in compound 3 and the protonated D-methionine molecules and (þ)-18C6H4 molecules in compound 4, respectively. 2.4. The supramolecular helical model, type 2-2 The asymmetric unit of compound DL-methioni- nium maleate (5) [26] contains a protonated DL-meth- ionine molecule (DLmethioninium molecule) (CH3Se CH2CH2CHNHþ 3 COOH) and a free maleate molecule (OOCCHCHCOO-) (Fig. 5a). The amino nitrogen (N1) from a DL-methioninium molecule acts as a m2-linker to connect the carboxylate oxygen atom (O5) and the carboxylate oxygen atom (O6) from two adjacent maleate molecules by two types of hydrogen bond interactions (N1eH4/O5, 2.040 Å, N1eO5, 2.913 Å, N1eH4/O5, 166.90 and N1eH3/O6, 2.187 Å, N1eO6, 2.972 Å, N1eH3/O6, 147.02 ) (Table S1) to develop the equable right-handed (P-Helix) and left-handed (M-Helix) supramolecular
Fig. 5. a) The asymmetric unit of compound 5; b) The right-handed supramolecular helical chains (P-helix) in compound 5; c) The left-handed supramolecular helical chains (M-helix); d) The 2D sheet in compound 5; e) The 3D packing picture in compound 5, viewed from b-axis.
helical chains (Fig. 5b and c). The carboxylate oxygen atom (O6) from a maleate molecule connects the amino nitrogen (N1) from a DL-methioninium molecule by a type of hydrogen bond interaction (N1eH2/O6, 1.926 Å, N1eO6, 2.812 Å, N1eH2/O6, 174.47 ) (Table S1). Thus, the left handed and right handed supramolecular helical chains are alternately packed to extent the 2D structure in compound 5 (Fig. 5d). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 5 (Fig. 5e). The supramolecular helical model of compound 5 is named type 2-2. There is a DL-methionine molecule in the asymmetric unit of compound 5. There are two kinds of supramolecular helical chains (the left-handed chain and the right-handed chain) constructed by part of protonated DL-methionine molecules and maleate molecules, which are enantiomer. The comment features of type 2e1 and type 2-2 are that there is a methionine molecule in the asymmetric unit of compounds 3, 4 and 5, and the supra-molecular helical chains are constructed by both methionine molecules and counterions rather than that in type 1-1 and type 1e2 constructed only by the meth-ionine molecules. 2.5. The supramolecular helical model, type 3 The asymmetric unit of compound L-methioninium perchlorate monohydrate (6) [27] contains a protonated L-methionine molecule (L-methioninium molecule) (CH3SCH2CH2CHNHþ 3 COOH) (green bounds), a L-methionine molecule (CH3SCH2CH2CHNHþ 3 COO ) (pink bounds), a free perchlorate ion (ClO4 ) and a water molecule (Fig. 6a). The water molecule (O9) acts as a m2-linker to connect the carboxylate oxygen atom (O5) and carboxylate oxygen atom (O5#4) from two L-methionine molecules (pink bounds) through two types of hydrogen bond interactions (O9e H24/O5, 1.915 Å, O9eO5, 2.705 Å, O9eH24/O5, 169.98 and O9eH25/O5#4, 1.950 Å, O9eO5#4, 2.759 Å, O9eH25/O5#4, 167.90 ) (Table S1) to develop the equable right-handed (P-Helix) supra-molecular helical chains (Fig. 6b). And, the perchlorate ion also acts as a m2-linker. The oxygen atom (O2) and the oxygen atom (O4) from a perchlorate ion connect. The amino nitrogen (N2) and the amino nitrogen (N2#5) from two L-methioninium molecules (green bounds) through two types of hydrogen bond interactions (N2eH14/O2, 2.199 Å, N2eO2, 2.909 Å, N2eH14/O2, 136.42 and N2#5-H16$$$O4, 2.510 Å, N2#5-O4, 2.997 Å, N2#5-H16$$$O4, 115.04 ) (Table S1) to develop the equable left-handed (M-Helix) supra-molecular helical chains (Fig. 6c). The amino nitrogen (N2) from the L-methioninium
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Fig. 6. a) The asymmetric unit of compound 6; b) The right-handed supramolecular helical chains (P-helix); c) The left -handed supramolecular helical chains (M-helix); d) The 2D sheet in compound 6; e) The 3D packing picture in compound 6, viewed from b-axis.
molecule (green bounds) connects the water molecule (O9) by a type of hydrogen bond interaction (N2eH16/O9, 2.007 Å, N2eO9, 2.797 Å, N2eH16/O9, 147.30 ). Thus, the left handed supramolecular helical chains and the right handed supramolecular helical chains are alternately packed to extent the 2D structure in compound 6 (Fig. 6d). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 6 (Fig. 6e). The supramolecular helical model of compound 6 is named type 3. There is a L-methionine molecule and a protonated L-methionine molecule in the asymme-tric unit of compound 6. And, there are two kinds of supramolecular helical chains (the right-handed chain and the left-handed chain) in compound 6. One is constructed by the L-methionine molecules and water molecules, and another one is constructed by the protonated L-methionine molecules and perchlorate ions. In type 3, we can find that both the L-methionine molecules and the protonated L-meth- ionine molecules can induce supramolecular helical chains.
Fig. 7. a) The asymmetric unit of compound 7; b) The right-handed supramolecular helical chains (P-helix) in compound 7; c) The left-handed supramolecular helical chains (M-helix) in compound 7; d) The 2D sheet in compound 7; e) The 3D packing picture in compound 7, viewed from b-axis.
supramolecular helical chains are alternately packed to extent the 2D structure in compound 7 (Fig. 7d). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 7 (Fig. 7e). The supramolecular helical model of compound 7 is named type 4. There is a D-methionine molecule in the asymmetric unit of compound 7. And, there are two kinds of supramolecular helical chains (two right-handed chains) in compound 7. One is constructed only by the D-methionine molecules while another one is only constructed by two (D)-mandelic acids. In type 4, the supramolecular helical chains constructed only by the counterions are found.
2.6. The supramolecular helical model, type 4 2.7. The supramolecular helical model, type 5 The asymmetric unit of compound (D)-methioninium (D)mandelate (D)-mandelic acid (7)28 contains a protonated Dmethionine molecule (D-methioninium molecule) (CH3SCH2CH2CHNHþ 3 COOH), a (D)- mandelate ion (green bounds) and two (D)-mandelic acids (light blue and dark blue bounds) (Fig. 7a). The amino nitrogen atom (N1) from a D-methioninium molecule connects the carboxylate oxygen atom (O2) from an adjacent one through a type of hydrogen bond interaction (N1eH9/O2, 2.470 Å, N1eO2, 2.932 Å, N1eH9/O2, 112.87 ) (Table S1) to develop the right-handed (P-Helix) supramolecular helical chains (Fig. 7b). And, the carboxylate oxygen atom (O4) and the hydroxyl oxygen atom (O8) from a (D)-mandelic. Acid (light blue) connect the carboxylate oxygen atom (O6) and the hydroxyl oxygen atom (O5) from a (D)-mandelic acid (dark blue bounds) through two types of hydrogen bond interactions (O6eH4/O4, 1.671 Å, O6eO4, 2.639 Å, O6eH4/O4, 162.63 and O5eH3/O8, 2.106 Å, O5eO8, 2.970 Å, O5eH3/O8, 178.73 ) (Table S1) to develop the equable right-handed (P-Helix) supramolecular helical chains (Fig. 7c). The hydroxyl oxygen atom (O8) from a (D)-mandelic acid (light blue bounds) connects the amino nitrogen atom (N1) from a D-methioninium molecule by a type of hydrogen bond interaction (N1eH8/O8, 2.058 Å, N1eO8, 2.923 Å, N1eH8/O8, 163.80 ). Thus, the two kinds of right handed
The asymmetric unit of compound L-methionine (þ)-18-crown6 tetracarboxylic acid ((þ)-18C6H4) (8) [25] contains a protonated L-methionine molecule (L-methioninium molecule) (CH3SCH2CH2CHNHþ 3 - COOH), a (þ)-18C6H4 molecule and a water molecule (Fig. 8a). The water molecule (O1) acts as a m3-linker. First, the water molecule (O1) connects the carboxylate oxygen atom (O9) and the carboxylate oxygen atom (O12) from two adjacent (þ)-18C6H4 molecules by two types of hydrogen bond interactions (O9eH23/O1, 1.575 Å, O9eO1, 2.582 Å, O9eH23/O1, 174.85 and O1eH3/O12, 2.102 Å, O1eO12, 2.840 Å, O1eH3/O12, 154.55 ) (Table S1) to develop equivalent right handed (P-Helix) supramolecular helical chains (Fig. 8b). Second, the water molecule (O1) connects the carboxylate oxygen atom (O15) by a type of hydrogen bond interaction (O1eH25/O15, 1.635 Å, O1eO15, 2.550 Å, O1eH25/O15, 158.58 ) to extent the 2D structure in compound 8 (Fig. 8c). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 8 (Fig. 8d). The supramolecular helical model of compound 8 is named type 5. There is a L-methionine molecule in the asymmetric unit of compound 8. And, there is a kind of supramolecular helical chain in compound 8, which is. Constructed only by (þ)-18C6H4 molecules and water
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((þ)-18C6H4) but with different methionine molecules (D-methionine molecule and L-methionine molecule), respectively, and they display different supramolecular helical models (type 2e1 and type 5), which may indicate that the chirality of methionine molecules may play important influences on the self-assembly of supramolecular helical chains. 4. The supramolecular helical chains in compounds 3 and 4 display the same supramolecular helical model (type 2e1) while compounds 3 and 4 contain different counterions and different methionine molecules (L- and D-methionine molecule), which may indicate that the supramolecular helical model may be influenced by many factors. Declaration of competing interest Fig. 8. a) The asymmetric unit of compound 8; b) The right-handed supramolecular helical chains (P-helix) in compound 8; c) The 2D sheet in compound 8; d) The 3D packing picture in compound 8, viewed from b-axis.
molecules. In type 5, the supramolecular helical chain is only constructed by the counterions while the L-methionine molecule does not participate in constructing supramolecular helical chain. 2.8. No supramolecular helical chain No supramolecular helical chain is found in compounds DLmethionine sulfate (9) [29,30], DL-meth- ioninium phosphoric acid (10) [31], DL-methioninium trichloroacetate (11) [32], Lmethionine hexafluorosilicate (12) [33]. It seems hard for the compounds with DL-methionine molecules to construct supramolecular helical chains. 3. Conclusions Twelve compounds of methionine with inorganic/organic acids (methionine-acid compounds) from the Cambridge Crystallographic Data Centre database before 2020 were discussed from the aspect of the way of methionine self-organizing into supramolecular helical chains. The supramolecular helical chains are found in eight methionine-acid compounds for the first time, which display various self-assembly models. The structure features and the laws of supramolecular helical chains self-assembly in methionine-acid compounds are drawn as follow: 1. The compounds with D-methionine molecules or L-methionine molecules: Compounds 2 (type 1e2), 3 (type 2e1), 6 (type 3), 8 (type 5) and 12 contain L-methionine molecules. Compounds 4 (type 2e1) and 7 (type 4) contain D-methionine molecules. In above compounds, only compound 12 does not contain supramolecular helical chain, which may indicate that it is easy for compounds with only D-methionine molecules or L-methionine molecules to construct supramolecular helical chains. And, both the D-methionine molecules and the L-methionine molecules can induce multiply models of supra-molecular helical chains. 2. The compounds with DL-methionine molecules: Compounds 1 (type 1-1), 5 (type 2-2), 9, 10 and 11 contain DL-methionine molecules. The right-handed and left-handed supramolecular helical chains coexist in the compounds 1 and 5 and they are enantiomer, and no supramolecular helical chain is found in compounds 9, 10 and 11, which may indicate that DL-methionine molecules will induce enantiomer supramolecular helical chain into compounds while it may be hard for DL-methionine molecules to induce supramolecular helical chains into compounds. 3. Compounds 4 and 8 contain the same counterions
There is no conflict to declare. Acknowledgements This work is financially supported by the China Postdoctoral Science Foundation (Grant No. 2018 M632640), Qingdao Postdoctoral Applied Research Project (2018103, 2018111), National College Students Innovation and Entrepreneurship Training Program (201910429007) and the FirstClass Discipline Project Funded by the Education Department of Shandong Province Postdoctoral Innovation Project (2019057). Appendix A. Supplementary data Supplementary data to this article can be found online at https://doi.org/10.1016/j.molstruc.2020.127847. References [1] F. Gan, R. Liu, F. Wang, P.G. Schultz, Functional replacement of histidine in proteins to generate noncanonical amino acid dependent organisms, J. Am. Chem. Soc. 140 (2018) 3829e3832. [2] R. Kumar, V. Mutreja, G. Sharma, S. Kumar, A. Ali, S.K. Mehta, P. Venugopalan, R. Kataria, S.C. Sahoo, The role of a weakly coordinating thioether groupin ligation controlled molecular self-assembliesand their inter-conversions in Ni(II) complexes of L -methionine derived ligand, New J. Chem. 43 (2019) 11222e11232. [3] C.L. Perrin, Y. Wu, Symmetry of hydrogen bonds in two enols in solution, J. Am. Chem. Soc. 141 (2019) 4103e4107. ni, T. Juha sz, M. Palko , G. Paragi, G.K. To th, [4] I. Nekkaa, D. Bogd an, T. G ati, S. Be € p, I.M. M F. Fülo andity, Flow- chemistry enabled efficient synthesis of b-peptides: backbone topology vs. helix formation, Chem. Commun. 55 (2019) 3061e3064. [5] C. Zheng, L. Yang, H. Li, H. Sun, X. Bi, Researches on the construction of supramolecular helical chains in crystallized b-alaninium sulfate/perchlorate compounds, J. Mol. Struct. 1177 (2019) 519e524. [6] C. Zheng, X. Bi, J. Ma, Y. Zhao, C. Gu, The self organizing of supramolecular helical chains in crystallized eighteen compounds of L-alanine with inorganic/ organic acids, J. Mol. Struct. 1202 (2020), 127382. [7] C. Zheng, H. Sun, J. Ma, X. Bi, Y. Tang, B. Shan, The achiral b-alanine self organizes into supramolecular helical chains in crystallized achiral b-alaninium inorganic/organic acid compounds, J. Mol. Struct. 1199 (2020), 126920. [8] A. Sharma, P. Tiwari, A.D. Konar, The dominant role of side chains in supramolecular double helical organisation in synthetic tripeptides, J. Mol. Struct. 1161 (2018) 44e54. [9] L.K. Joy, M. George, J. Alex, A. Aravind, D. Sajan, G. Vinitha, Twisted intramolecular charge transfer investigation of semi organic L-Glutamic acid hydrochloride single crystal for organic light-emitting and optical limiting applications, J. Mol. Struct. 1156 (2018) 733e744. [10] M. Chahkandi, M.H. Bhatti, U. Yunus, M. Nadeem, M.N. Tahir, Crystalline network study of new N-phthaloyl- b-Alanine with benzimidazole, cocrystal: computational consideration & free radical scavenging activity, J. Mol. Struct. 1191 (2019) 225e236. [11] S. Guha, M.G.B. Drew, A. Banerjee, A new molecular scaffold for the formation of supramolecular peptide double helices: the crystallographic insight, Org. Lett. 97 (2007) 1347e1350. [12] M. Chahkandi, M.H. Bhatti, U. Yunus, N. Rehman, M. Zakria, Novel cocrystal of N-phthaloyl-b-alanine with 2,2-bipyridyl: synthesis, computational and free
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Journal of Molecular Structure journal homepage: http://www.elsevier.com/locate/molstruc
The self-assembly of supramolecular helical chains in crystallized compounds of methionine with inorganic/organic acids Chunying Zheng a, *, Caiwei Liu b, Xinyang Zhang a a b
School of Environmental and Municipal Engineering, Qingdao University of Technology, Qingdao, 266033, PR China College of Civil Engineering, Qingdao University of Technology, Qingdao, 266033, PR China
a r t i c l e i n f o
a b s t r a c t
Article history: Received 25 December 2019 Received in revised form 29 January 2020 Accepted 3 February 2020 Available online 4 February 2020
In this paper, the supramolecular helical chains are found in eight crystallized compounds of methionine with inorganic/organic acids for the first time. The self-assembly and the components of supramolecular helical chains are analyzed in detail, and the supramolecular helical features are summarized in this contribution, which may throw light on the nature of biomolecular aggregation patterns and intermolecular interactions about methionine compounds. © 2020 Elsevier B.V. All rights reserved.
1. Introduction Weak interactions including van der Waals, p-p interactions and various hydrogen bonds play an important role in the crystal packing of compounds [1e8]. Amino acids usually exist in the form of zwitterions that contain protonated amino groups (-NHþ 3 ) and deprotonated carboxylic acid groups (-COO-), which induce amino acids to be natural building blocks for supramolecular H-bonding networks [9e14] and may introduce novel biological, physical and chemical properties [15,16]. Methionine is a straight-chain aliphatic-amino acid and is one of few sulfur-containing amino acids [17]. Methionine shows an important antioxidant because of its sulfur group, and is also very important as a donor of an active methyl group [18,19]. Methionine is buried within proteins, and contributes to the synthesis of many important substances, and is indispensable for normal maintenance, metabolism and growth of body tissues, and is involved in many very important processes, such as the transfer of methyl groups and sulfur metabolism and the initiation of translation of messenger RNA [20]. Previous reports about crystallized compounds of methionine with inorganic/organic acids (methionine -acid compounds) mainly focus on studying the conformation and hydrogen-bonding features of methionine in the presence of inorganic/organic acids, which are expected to provide useful information regarding biomolecular aggregation patterns [21e33]. Rare report is about the self-assembly of supramolecular helical chains in methionine-acid
compounds. The supramolecular helical chain is of prime importance for understanding of the origins of life, the potential chemical properties and the potential physical properties [34e38]. And, understanding the self-organizing way of supramolecular helical chain is still an essential question for chemists [39e42]. In this paper, we analyzed twelve compounds of methionine with inorganic/organic acids (methionine-acid compounds) from the Cambridge Crystallographic Data Centre database before 2020 in the aspect of the way of methionine self-organizing into supramolecular helical chains. The supramolecular helical chains were found in eight methionine-acid compounds for the first time. The supramolecular helical models and the possible influencing factors on the self-assembly of supramolecular helical chains in methionine-acid compounds were discussed and summarized in detail. 2. Results and discussion In this paper, according to the components of supramolecular helical chains in each compound, the supramolecular helical models in the eight methionine-acid compounds are classified into five types, named type 1, type 2, type 3, type 4 and type 5. And then, according to the number and the chirality of supramolecular helical chains in each compound, the supramolecular helical models are further classified into seven types, named type 1-1, type 1e2, type 2e1, type 2-2, type 3, type 4 and type 5. 2.1. The supramolecular helical model, type 1-1
* Corresponding author. E-mail address: [email protected] (C. Zheng). https://doi.org/10.1016/j.molstruc.2020.127847 0022-2860/© 2020 Elsevier B.V. All rights reserved.
The asymmetric unit of compound DL-methioni- nium nitrate
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Fig. 1. a) The asymmetric unit of compound 1; b) The right-handed supramolecular helical chains (P-helix) in compound 1; c) The left-handed supramolecular helical chains (M-helix) in compound 1; d) The 3D packing picture in compound 1, viewed from b-axis.
(1) [22] contains a protonated DL-methionine molecule (DLmethioninium molecule) (CH3SCH2CH2CHNHþ 3 COOH) and a free nitrate ion (NO 3 ) (Fig. 1a). The carboxylate oxygen atom (O2) of a DL-methioninium molecule connects the oxygen atom (O2#1) from an adjacent DL-methioninium molecule by a type of hydrogen bond interaction (O2e H12/O2#1, 2.972 Å, O2eO2#1, 3.479 Å, O2e H12/O2#1, 119.10 ) (Table S1) to develop equivalent right handed (P-Helix) and left handed (M-Helix) supramolecular helical chains (Fig. 1b and c). The left handed supramolecular helical chains and the right handed ones are alternately packed by van der Waals to extent the 3D structure in compound 1 (Fig. 1d). The supramolecular helical model of compound 1 is named type 1-1. There is only a DL-methionine molecule in the asymmetric unit of compound 1. There are two kinds of supramolecular helical chains (the left-handed chain and the right-handed chain) in compound 1. And, the two supramolecular helical chains are composed only by the self-organizing of DL-methionine molecules, and the two supramolecular helical chains are enantiomer.
2.2. The supramolecular helical model, type 1-2 The asymmetric unit of compound L-methioninium nitrate (2) [23] contains two protonated L-meth- ionine molecules (L-methionine molecules) (pink and light blue bounds) (CH3SCH2CH2CHNHþ 3 COOH) and two free nitrate ions (NO3 ) (Fig. 2a). The carboxylate oxygen atom (O1) from a L-methionine molecule (pink bounds) is connected to the amino nitrogen (N1) from an adjacent one by a type of hydrogen bond interaction
Fig. 2. a) The asymmetric unit of compound 2; b) and c) The left-handed supramolecular helical chains (M-helix) in compound 2; d) The 2D sheet in compound 2; e) The 3D packing picture in compound 2, viewed from b-axis.
(N1eH5/O1 ¼ 2.083 Å, N1eO1, 2.858 Å, N1eH5/O1. 144.96 (Table S1) to develop equable left handed (M-Helix) supramolecular helical chains (Fig. 1b). Similarly, the carboxylate oxygen atom (O3) from a L-methionine molecule (light blue bounds) is connected to the amino nitrogen (N2) from an adjacent one by a type of hydrogen bond interaction (N2eH17/O3, 2.097 Å, N2eO3, 2.877 Å, N2eH17/O3, 144.14 ) (Table S1) to develop another left handed (M-Helix) supramolecular helical chains (Fig. 1c). The oxygen atom (O9) and oxygen atom (O10) from a nitrate ion with N4 atom connect a amino nitrogen atom (N2) from a L-methionine molecule (light blue bounds) and a carboxylate oxygen atom (O2) from a L-methionine molecule (pink bounds) by two types of hydrogen bond interactions (N2eH16/O9, 2.002 Å, N2eO9, 2.840 Å, N2eH16/O9, 156.51 and O2e H1/O10, 1.895 Å, O2eO10, 2.663 Å, O2eH1/O10, 168.69 ), respectively. Thus, the two kinds of left handed supramolecular helical chains are connected alternately to give rise to the 2D structure in compound 2 (Fig. 2d). The nitrate ion with N3 atom connect the amino nitrogen (N1) from a L-methionine molecule (pink bounds) by a type of hydrogen bond interaction (N1eH4/O7, 2.008 Å, N1eO7, 2.854 Å, N1eH4/O7, 158.45 ). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 2 (Fig. 2e). The supramolecular helical model of compound 2 is named type 1e2. There are two L-methionine molecules in the asymmetric unit of compound 2. There are also two kinds of supramolecular helical chains. And they are constructed only by the self-organizing of two L-methionine molecules, respectively, but they are not enantiomer. The comment features of type 1-1 and type 1e2 are that compounds 1 and 2 contain two kinds of the supramolecular helical chains and they are constructed only by the methionine molecules. 2.3. The supramolecular helical model, type 2-1 The asymmetric unit of compound L-methioninium chloride (3) [24] contains a protonated L-meth- ionine molecule (L-methioninium molecule) (CH3Se CH2CH2CHNHþ 3 COOH) and a free chloride ion (Cl) (Fig. 3a). The chloride ion (Cl1) acts as a m3-linker. First, the chloride ion (Cl1) connects the amino nitrogen (N1) and the amino nitrogen (N1#2) from two L-methioninium molecules through two
Fig. 3. a) The asymmetric unit of compound 3; b) The left-handed supramolecular helical chains (M-helix) in compound 3; c) The 2D sheet in compound 3; d) The 3D packing picture in compound 3, viewed from a-axis.
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Fig. 4. a) The asymmetric unit of compound 4; b) The left-handed supramolecular helical chains (M-helix) in compound 4; c) The 3D packing picture in compound 4, viewed from b-axis.
types of hydrogen bond interactions (N1eH12/Cl1, 2.512 Å, N1eCl1, 2.854 Å, N1eH12/Cl1, 158.45 and N1#2-H11$$$Cl1, 2.396 Å, N1#2-Cl1, 2.838 Å, N1#2-H11$$$Cl1, 179.450 ) (Table S1) to develop the equable left-handed (M-Helix) supramolecular helical chains (Fig. 3b). Second, the chloride ion (Cl1) connects the amino nitrogen (N1#3) from another. L-methioninium molecule through a type of hydrogen bond interaction (N1#3-H10$$$Cl1, 2.364 Å, N1#3-Cl1, 3.184 Å, N1#3H10$$$Cl1, 174.74 ) (Table S1) to develop the 2D sheets in compound 3 (Fig. 3c). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 3 (Fig. 3d). The asymmetric unit of compound D-methionine (þ)-18-crown6 tetracarboxylic acid ((þ)-18C6H4) (4) [25] contains a protonated D-methionine molecule (D-methioninium molecule) (CH3SCH2CH2CHNHþ 3 - COOH), a (þ)-18C6H4 molecule and three water molecules (Fig. 4a). The carboxylate oxygen atom (O18) and the amino nitrogen (N1) from a D-methioninium molecule connect the carboxylate oxygen atom (O17) and the carboxylate oxygen atom (O10) from two adjacent (þ)-18C6H4 molecules by two types of hydrogen bond interactions (O18eH28/O17, 1.546 Å, O18eO17, 2.555 Å, O18e H28/O17,155.40 and N1eH24/O10, 2.063 Å, N1e O10, 3.000 Å, N1eH24/O10, 168.24 ) (Table S1) to develop equivalent left handed (M-Helix) supramolecular helical chains (Fig. 4b). The left handed supramolecular helical chains are parallelly packed by van der Waals to extent the 3D structure in compound 4 (Fig. 4c). The supramolecular helical model of compounds 3 and 4 is named type 2e1. There is a methionine molecule in the asymmetric unit of compounds 3 and 4. There is only a kind of supramolecular helical chain in compound 3 and compound 4, which is constructed by part of protonated L-methionine molecules and free chloride ions in compound 3 and the protonated D-methionine molecules and (þ)-18C6H4 molecules in compound 4, respectively. 2.4. The supramolecular helical model, type 2-2 The asymmetric unit of compound DL-methioni- nium maleate (5) [26] contains a protonated DL-meth- ionine molecule (DLmethioninium molecule) (CH3Se CH2CH2CHNHþ 3 COOH) and a free maleate molecule (OOCCHCHCOO-) (Fig. 5a). The amino nitrogen (N1) from a DL-methioninium molecule acts as a m2-linker to connect the carboxylate oxygen atom (O5) and the carboxylate oxygen atom (O6) from two adjacent maleate molecules by two types of hydrogen bond interactions (N1eH4/O5, 2.040 Å, N1eO5, 2.913 Å, N1eH4/O5, 166.90 and N1eH3/O6, 2.187 Å, N1eO6, 2.972 Å, N1eH3/O6, 147.02 ) (Table S1) to develop the equable right-handed (P-Helix) and left-handed (M-Helix) supramolecular
Fig. 5. a) The asymmetric unit of compound 5; b) The right-handed supramolecular helical chains (P-helix) in compound 5; c) The left-handed supramolecular helical chains (M-helix); d) The 2D sheet in compound 5; e) The 3D packing picture in compound 5, viewed from b-axis.
helical chains (Fig. 5b and c). The carboxylate oxygen atom (O6) from a maleate molecule connects the amino nitrogen (N1) from a DL-methioninium molecule by a type of hydrogen bond interaction (N1eH2/O6, 1.926 Å, N1eO6, 2.812 Å, N1eH2/O6, 174.47 ) (Table S1). Thus, the left handed and right handed supramolecular helical chains are alternately packed to extent the 2D structure in compound 5 (Fig. 5d). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 5 (Fig. 5e). The supramolecular helical model of compound 5 is named type 2-2. There is a DL-methionine molecule in the asymmetric unit of compound 5. There are two kinds of supramolecular helical chains (the left-handed chain and the right-handed chain) constructed by part of protonated DL-methionine molecules and maleate molecules, which are enantiomer. The comment features of type 2e1 and type 2-2 are that there is a methionine molecule in the asymmetric unit of compounds 3, 4 and 5, and the supra-molecular helical chains are constructed by both methionine molecules and counterions rather than that in type 1-1 and type 1e2 constructed only by the meth-ionine molecules. 2.5. The supramolecular helical model, type 3 The asymmetric unit of compound L-methioninium perchlorate monohydrate (6) [27] contains a protonated L-methionine molecule (L-methioninium molecule) (CH3SCH2CH2CHNHþ 3 COOH) (green bounds), a L-methionine molecule (CH3SCH2CH2CHNHþ 3 COO ) (pink bounds), a free perchlorate ion (ClO4 ) and a water molecule (Fig. 6a). The water molecule (O9) acts as a m2-linker to connect the carboxylate oxygen atom (O5) and carboxylate oxygen atom (O5#4) from two L-methionine molecules (pink bounds) through two types of hydrogen bond interactions (O9e H24/O5, 1.915 Å, O9eO5, 2.705 Å, O9eH24/O5, 169.98 and O9eH25/O5#4, 1.950 Å, O9eO5#4, 2.759 Å, O9eH25/O5#4, 167.90 ) (Table S1) to develop the equable right-handed (P-Helix) supra-molecular helical chains (Fig. 6b). And, the perchlorate ion also acts as a m2-linker. The oxygen atom (O2) and the oxygen atom (O4) from a perchlorate ion connect. The amino nitrogen (N2) and the amino nitrogen (N2#5) from two L-methioninium molecules (green bounds) through two types of hydrogen bond interactions (N2eH14/O2, 2.199 Å, N2eO2, 2.909 Å, N2eH14/O2, 136.42 and N2#5-H16$$$O4, 2.510 Å, N2#5-O4, 2.997 Å, N2#5-H16$$$O4, 115.04 ) (Table S1) to develop the equable left-handed (M-Helix) supra-molecular helical chains (Fig. 6c). The amino nitrogen (N2) from the L-methioninium
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Fig. 6. a) The asymmetric unit of compound 6; b) The right-handed supramolecular helical chains (P-helix); c) The left -handed supramolecular helical chains (M-helix); d) The 2D sheet in compound 6; e) The 3D packing picture in compound 6, viewed from b-axis.
molecule (green bounds) connects the water molecule (O9) by a type of hydrogen bond interaction (N2eH16/O9, 2.007 Å, N2eO9, 2.797 Å, N2eH16/O9, 147.30 ). Thus, the left handed supramolecular helical chains and the right handed supramolecular helical chains are alternately packed to extent the 2D structure in compound 6 (Fig. 6d). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 6 (Fig. 6e). The supramolecular helical model of compound 6 is named type 3. There is a L-methionine molecule and a protonated L-methionine molecule in the asymme-tric unit of compound 6. And, there are two kinds of supramolecular helical chains (the right-handed chain and the left-handed chain) in compound 6. One is constructed by the L-methionine molecules and water molecules, and another one is constructed by the protonated L-methionine molecules and perchlorate ions. In type 3, we can find that both the L-methionine molecules and the protonated L-meth- ionine molecules can induce supramolecular helical chains.
Fig. 7. a) The asymmetric unit of compound 7; b) The right-handed supramolecular helical chains (P-helix) in compound 7; c) The left-handed supramolecular helical chains (M-helix) in compound 7; d) The 2D sheet in compound 7; e) The 3D packing picture in compound 7, viewed from b-axis.
supramolecular helical chains are alternately packed to extent the 2D structure in compound 7 (Fig. 7d). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 7 (Fig. 7e). The supramolecular helical model of compound 7 is named type 4. There is a D-methionine molecule in the asymmetric unit of compound 7. And, there are two kinds of supramolecular helical chains (two right-handed chains) in compound 7. One is constructed only by the D-methionine molecules while another one is only constructed by two (D)-mandelic acids. In type 4, the supramolecular helical chains constructed only by the counterions are found.
2.6. The supramolecular helical model, type 4 2.7. The supramolecular helical model, type 5 The asymmetric unit of compound (D)-methioninium (D)mandelate (D)-mandelic acid (7)28 contains a protonated Dmethionine molecule (D-methioninium molecule) (CH3SCH2CH2CHNHþ 3 COOH), a (D)- mandelate ion (green bounds) and two (D)-mandelic acids (light blue and dark blue bounds) (Fig. 7a). The amino nitrogen atom (N1) from a D-methioninium molecule connects the carboxylate oxygen atom (O2) from an adjacent one through a type of hydrogen bond interaction (N1eH9/O2, 2.470 Å, N1eO2, 2.932 Å, N1eH9/O2, 112.87 ) (Table S1) to develop the right-handed (P-Helix) supramolecular helical chains (Fig. 7b). And, the carboxylate oxygen atom (O4) and the hydroxyl oxygen atom (O8) from a (D)-mandelic. Acid (light blue) connect the carboxylate oxygen atom (O6) and the hydroxyl oxygen atom (O5) from a (D)-mandelic acid (dark blue bounds) through two types of hydrogen bond interactions (O6eH4/O4, 1.671 Å, O6eO4, 2.639 Å, O6eH4/O4, 162.63 and O5eH3/O8, 2.106 Å, O5eO8, 2.970 Å, O5eH3/O8, 178.73 ) (Table S1) to develop the equable right-handed (P-Helix) supramolecular helical chains (Fig. 7c). The hydroxyl oxygen atom (O8) from a (D)-mandelic acid (light blue bounds) connects the amino nitrogen atom (N1) from a D-methioninium molecule by a type of hydrogen bond interaction (N1eH8/O8, 2.058 Å, N1eO8, 2.923 Å, N1eH8/O8, 163.80 ). Thus, the two kinds of right handed
The asymmetric unit of compound L-methionine (þ)-18-crown6 tetracarboxylic acid ((þ)-18C6H4) (8) [25] contains a protonated L-methionine molecule (L-methioninium molecule) (CH3SCH2CH2CHNHþ 3 - COOH), a (þ)-18C6H4 molecule and a water molecule (Fig. 8a). The water molecule (O1) acts as a m3-linker. First, the water molecule (O1) connects the carboxylate oxygen atom (O9) and the carboxylate oxygen atom (O12) from two adjacent (þ)-18C6H4 molecules by two types of hydrogen bond interactions (O9eH23/O1, 1.575 Å, O9eO1, 2.582 Å, O9eH23/O1, 174.85 and O1eH3/O12, 2.102 Å, O1eO12, 2.840 Å, O1eH3/O12, 154.55 ) (Table S1) to develop equivalent right handed (P-Helix) supramolecular helical chains (Fig. 8b). Second, the water molecule (O1) connects the carboxylate oxygen atom (O15) by a type of hydrogen bond interaction (O1eH25/O15, 1.635 Å, O1eO15, 2.550 Å, O1eH25/O15, 158.58 ) to extent the 2D structure in compound 8 (Fig. 8c). The 2D sheets are parallelly packed by van der Waals to extent the 3D structure in compound 8 (Fig. 8d). The supramolecular helical model of compound 8 is named type 5. There is a L-methionine molecule in the asymmetric unit of compound 8. And, there is a kind of supramolecular helical chain in compound 8, which is. Constructed only by (þ)-18C6H4 molecules and water
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5
((þ)-18C6H4) but with different methionine molecules (D-methionine molecule and L-methionine molecule), respectively, and they display different supramolecular helical models (type 2e1 and type 5), which may indicate that the chirality of methionine molecules may play important influences on the self-assembly of supramolecular helical chains. 4. The supramolecular helical chains in compounds 3 and 4 display the same supramolecular helical model (type 2e1) while compounds 3 and 4 contain different counterions and different methionine molecules (L- and D-methionine molecule), which may indicate that the supramolecular helical model may be influenced by many factors. Declaration of competing interest Fig. 8. a) The asymmetric unit of compound 8; b) The right-handed supramolecular helical chains (P-helix) in compound 8; c) The 2D sheet in compound 8; d) The 3D packing picture in compound 8, viewed from b-axis.
molecules. In type 5, the supramolecular helical chain is only constructed by the counterions while the L-methionine molecule does not participate in constructing supramolecular helical chain. 2.8. No supramolecular helical chain No supramolecular helical chain is found in compounds DLmethionine sulfate (9) [29,30], DL-meth- ioninium phosphoric acid (10) [31], DL-methioninium trichloroacetate (11) [32], Lmethionine hexafluorosilicate (12) [33]. It seems hard for the compounds with DL-methionine molecules to construct supramolecular helical chains. 3. Conclusions Twelve compounds of methionine with inorganic/organic acids (methionine-acid compounds) from the Cambridge Crystallographic Data Centre database before 2020 were discussed from the aspect of the way of methionine self-organizing into supramolecular helical chains. The supramolecular helical chains are found in eight methionine-acid compounds for the first time, which display various self-assembly models. The structure features and the laws of supramolecular helical chains self-assembly in methionine-acid compounds are drawn as follow: 1. The compounds with D-methionine molecules or L-methionine molecules: Compounds 2 (type 1e2), 3 (type 2e1), 6 (type 3), 8 (type 5) and 12 contain L-methionine molecules. Compounds 4 (type 2e1) and 7 (type 4) contain D-methionine molecules. In above compounds, only compound 12 does not contain supramolecular helical chain, which may indicate that it is easy for compounds with only D-methionine molecules or L-methionine molecules to construct supramolecular helical chains. And, both the D-methionine molecules and the L-methionine molecules can induce multiply models of supra-molecular helical chains. 2. The compounds with DL-methionine molecules: Compounds 1 (type 1-1), 5 (type 2-2), 9, 10 and 11 contain DL-methionine molecules. The right-handed and left-handed supramolecular helical chains coexist in the compounds 1 and 5 and they are enantiomer, and no supramolecular helical chain is found in compounds 9, 10 and 11, which may indicate that DL-methionine molecules will induce enantiomer supramolecular helical chain into compounds while it may be hard for DL-methionine molecules to induce supramolecular helical chains into compounds. 3. Compounds 4 and 8 contain the same counterions
There is no conflict to declare. Acknowledgements This work is financially supported by the China Postdoctoral Science Foundation (Grant No. 2018 M632640), Qingdao Postdoctoral Applied Research Project (2018103, 2018111), National College Students Innovation and Entrepreneurship Training Program (201910429007) and the FirstClass Discipline Project Funded by the Education Department of Shandong Province Postdoctoral Innovation Project (2019057). Appendix A. Supplementary data Supplementary data to this article can be found online at https://doi.org/10.1016/j.molstruc.2020.127847. References [1] F. Gan, R. Liu, F. Wang, P.G. Schultz, Functional replacement of histidine in proteins to generate noncanonical amino acid dependent organisms, J. Am. Chem. Soc. 140 (2018) 3829e3832. [2] R. Kumar, V. Mutreja, G. Sharma, S. Kumar, A. Ali, S.K. Mehta, P. Venugopalan, R. Kataria, S.C. Sahoo, The role of a weakly coordinating thioether groupin ligation controlled molecular self-assembliesand their inter-conversions in Ni(II) complexes of L -methionine derived ligand, New J. Chem. 43 (2019) 11222e11232. [3] C.L. Perrin, Y. Wu, Symmetry of hydrogen bonds in two enols in solution, J. Am. Chem. Soc. 141 (2019) 4103e4107. ni, T. Juha sz, M. Palko , G. Paragi, G.K. To th, [4] I. Nekkaa, D. Bogd an, T. G ati, S. Be € p, I.M. M F. Fülo andity, Flow- chemistry enabled efficient synthesis of b-peptides: backbone topology vs. helix formation, Chem. Commun. 55 (2019) 3061e3064. [5] C. Zheng, L. Yang, H. Li, H. Sun, X. Bi, Researches on the construction of supramolecular helical chains in crystallized b-alaninium sulfate/perchlorate compounds, J. Mol. Struct. 1177 (2019) 519e524. [6] C. Zheng, X. Bi, J. Ma, Y. Zhao, C. Gu, The self organizing of supramolecular helical chains in crystallized eighteen compounds of L-alanine with inorganic/ organic acids, J. Mol. Struct. 1202 (2020), 127382. [7] C. Zheng, H. Sun, J. Ma, X. Bi, Y. Tang, B. Shan, The achiral b-alanine self organizes into supramolecular helical chains in crystallized achiral b-alaninium inorganic/organic acid compounds, J. Mol. Struct. 1199 (2020), 126920. [8] A. Sharma, P. Tiwari, A.D. Konar, The dominant role of side chains in supramolecular double helical organisation in synthetic tripeptides, J. Mol. Struct. 1161 (2018) 44e54. [9] L.K. Joy, M. George, J. Alex, A. Aravind, D. Sajan, G. Vinitha, Twisted intramolecular charge transfer investigation of semi organic L-Glutamic acid hydrochloride single crystal for organic light-emitting and optical limiting applications, J. Mol. Struct. 1156 (2018) 733e744. [10] M. Chahkandi, M.H. Bhatti, U. Yunus, M. Nadeem, M.N. Tahir, Crystalline network study of new N-phthaloyl- b-Alanine with benzimidazole, cocrystal: computational consideration & free radical scavenging activity, J. Mol. Struct. 1191 (2019) 225e236. [11] S. Guha, M.G.B. Drew, A. Banerjee, A new molecular scaffold for the formation of supramolecular peptide double helices: the crystallographic insight, Org. Lett. 97 (2007) 1347e1350. [12] M. Chahkandi, M.H. Bhatti, U. Yunus, N. Rehman, M. Zakria, Novel cocrystal of N-phthaloyl-b-alanine with 2,2-bipyridyl: synthesis, computational and free
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