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Designation and Schematic Structure of Gangliosides and Allied Glycosphingolipids
XI
Designation and Schematic Structure of Gangliosides and Allied Glycosphingolipids Lars Svennerholm Depurtment of Clinical Neuroscience, Section of Psychtarn and Neitrochemistn. University of Goteborg. Goteborg. Sweden
With gangliosides and other higher glycosphingolipids naming problems arise from the complexity of the carbohydrate moiety of these compounds. The systematic names of the oligosaccharides linked to the lipophilic portion, i.e. ceramide, are so cumbersome that they cannot be used for oral communication. This difficulty has been overcome by creating suitable trivial names for the parent oligosaccharides, with the prefixes ganglio-, globoand lacto- to which the number of monosaccharides in the oligosaccharide is indicated by the suffixes -triaose, -tetraose, etc. (IUPAC-IUB, 1977) (Table I). Klenk ( 1942) defined ganglioside as a complex glycosphingolipid containing sialic acid. When it was discovered that brain tissue contained several gangliosides (Svennerholm, 1955) with varying number of sialic acids we suggested the generic terms mono-, di-, and trisialogangliosides (Svennerholm and Raal, 1962) which were easily accepted. It was, however, much more difficult to agree about a common system of trivial names or symbols for the various gangliosides and most investigators preferred to introduce their own designation. For more than 10 years most ganglioside conferences devoted time for intense debates about the most appropriate designations of the various gangliosides. Today, the code system suggested by Svennerholm in 1963 and continuously extended (Svennerholm, 1980, 1988) is generally accepted for gangliosides of the ganglio series, while there is still no general agreement about the designation of gangliosides of the lactoseries. The designations suggested in 1963 were based on the findings that brain tissue contained four major gangliosides of the ganglio series with a tetraose chain of neutral sugars. They were designated to belong to the GI series where G stands for ganglio. The four gangliosides differed with regard to the number of sialic acids where M, D, and T stood for mono-, di-, and tri-sialyl groups. There were two disialogangliosides, GDla and GDlb, and that one which contained a disialylgroup at the internal galactose was designated b (Table 11). When gangliosides of the ganglio series with three sialic acids linked to the internal galactose were detected, they were designated to belong to the c series. When the biosynthesis of the gangliosides of the ganglio series has been finally settled it is evident that the designation of an a, b and c series predicted the crucial role of the sialytransferases in the ganglioside metabolism (Van Echten and Sandhoff, 1993). Gangliosides lacking the terminal galactose were given number 2 and when lacking the disaccharide galactosyl-N-acetylgalactosaminenumber 3. We have suggested the symbol cisGM 1 for the monosialogangliotetraosylceramide in which the sialyl group is attached to the terminal galactose. Some researchers have unfortunately already used the designation of G M l b for this ganglioside, but b is already used to designate gangliosides with a disialyl group attached to the internal galactose. The name G M l b ought to be abandoned. Differences in linkage (e.g. 1 + 4 versus 1 + 3) in otherwise identical sequences are in general indicated by ‘iso’ used as a prefix. We have used it in the nomenclature for the lactoseries gangliosides (Table 111). The designation of gangliosides of the lactoseries follows the principal for gangliosides of the ganglio series. We have used the term LMl for the sialyllactotetraosyl ceramide in which the terminal linkage is f3l -4, because it
XI1
occurs more abundantly in the nervous system and other organs under physiological conditions. Is0 LM1 is used for the ganglioside with a terminal f3l + 3 linkage. The designation paragloboside is still used for the lactotetraosylceramide. This term was given to the glycolipids when its chemical structure was unknown, but para means chemically related to or derived from (New Webster’s Dictionary, 1992) and it will be equally incorrect to continue to use the name paragloboside for lactotetraosylceramide as to use strandin (Folch-Pi, 1951) for ganglioside. Further, I have also suggested the short symbols LKl and HexLKl for the two glucuronic acid-containing glycosphingolipids of the lactotetraose series (L) since they occur in killer cells (K) and will react with the HNK-1 antibody (Table IV).
References Folch, J., Arsove, S. and Meath. J.A. (1951) Isolation of brain strandin, a new type of large molecule tissue component. J. B i d . Chem., 191: 819-830. IUPAC-IUB Commission on Biochemical Nomenclature (CBN) (1977) The Nomenclature of Lipids. Eur. J . Biochern., 79: 11-21, Klenk, E. (1942) Uber die Ganglioside, eine neue Gruppe von zucherhaltigen Gehirnlipoiden. Hoppe-Seyfer’sZ. fhysiof. Chem.. 273: 76-86. New Webster’s Dictionary and the Thesaurus of the English Language ( 1 992) Lexicon Publications Inc., Daubury, CT. Svennerholm, L. (1956) Composition of gangliosides from human brain. Nuture. 177: 524525. Svennerholm. L. (1963) Chromatographic separation of human brain gangliosides. J . Neurochem., 10: 613423. Svennerholm, L. (1980) Ganglioside designation. In: L. Svennerholm, P. Mandel, H. Dreyfus and P.F. Urban (Eds.) Structure and Function ofcangliosides. Adv. Exp. Med. Biol., Vol 125. Plenum Press, New York, pp. 11. Svennerholm, L. (1988) Immunological and tumoral aspects of gangliosides. In: R.W., Ledeen, E.L.. Hogan, G., Tettamanti, A.J., Yates and R.K., Yu. (Eds.) New Trends in Ganglioside Reseurch, Fidia Research Series, Vol 14. Liviana Press, Padova. pp. 135-150. Svennerholm, L. and Raal, A. (1961) Composition of brain gangliosides. Biochem. Biophvs. Actu, 53: 422424. Van Echten, G. and Sandhoff, K. (1993) Ganglioside metabolism: enzymology, topology and regulation, J. Biol. Chem., 268: 5341-5344.
TABLE I Names and abbreviations of neutral glycosphingolipids Structure GalNAcPl+ 4GalP 1 4GlcCer 3GalNAcP 1 + 4GalP I + 4GIcCer -+
GalP I
-+
GalNAcP 1
-
Gala 1 + 4GalP 1 -+ 4GlcCer 3Gala 1 -+ 4GalP 1 -+ 4GlcCer
GlcNAcP 1 + 3GalP 1 -+ 4GlcCer GalP 1 -+ 4GLcNAcP 1 + 3GalP 1 4GlcCer GalP 1 3GlcNAcP 1 + 3GalP I 4GlcCer -+
-+
-+
Trivial name of oligosaccharide
Designation of glycosphingolipid
Gangliotriaose Gangliotetraose
GgOse,Cer GgOse,Cer
Globotriaose Globotetraose
GbOse,Cer GbOse,Cer
Lactotriaose Lactotetraose isoLactotetraose
LcOse,Cer LcOse,Cer isoLcOse,Cer
TABLE I1 Designation and schematic structure of ganglioseries gangliosides of biological interest. Schematic structure
Designation -
Svennerholm IUPAC-IUB (1977) (1963, 1980) GM4 GM3 GM2 GM 1 cis GMI ( * ) FUC-GM1 GD3 GD2 GDla GDIb Fuc-GD 1b GT3 GTla GTlb GTI c GQlb GQlc GPlb GPlc
I’NeuAc-GalCer II’Neu Ac-LacCer
NeuAca2 + 3GalP 1 + 1 ‘Cer NeuAca2 + 3GalPI +4Glc@I + 1’Cer II'Neu Ac-GgOse,Cer ~I+ GalNAcPl+4(NeuAca2 + 3) ~ “ ~ G a l ~ l + 4 G l cI‘Cer II’NeuAc-GgOse,Cer Gal,PI +3GalNAcPI +4(NeuAca2-+3)GalPI +4GlcPI + I’Cer WNeuAc-GgOse,Ger NeuAca2+3GalPI +3GalNAcPI -4GalPI -4GlcPI + I‘Cer IV’Fuc,II’NeuAc-GgOse,Cer Fucal + 2GalP 1 + 3GalNAcP I + 4(NeuAca2 3)GalPI +4GlcPI + 1‘Cer II’(NeuAc)Z-LacCer NeuAca2 + 8NeuAca2 + 3GalPl+ 4GlcPI + 1‘Cer GalNAcP 1 4(Neua2 + 8NeuAca2 + 3)GalP1 +4GlcP 1 + 1‘Cer I13(NeuAc)2-GgOse,Cer IV’NeuAc,II’NeuAc-GgOse,Cer NeuAca2 + 3GalP 1 + 3GalNAcP 1 +4(NeuAca2 + 3)GalP I +4GlcP 1 + 1 ‘Cer GalPl+ 3GalNAcPI +4(NeuAca2 + 8NeuAca2 3)GalPI +4GlcPI + 1‘Cer II’(NeuAc),-GgOse,Cer IV1Fuc,11’(NeuAc)2-GgOse,Cer I’Cer Fucal+2GalPI +3GalNAc~1+4(NeuAca2+8NeuAca2+3)Gal~l-+4Glc~l+ II’(NeuAc),-LacCer NeuAca2 + 8NeuAca2 + 8NeuAca2 + 3GalP 1 +4GlcPI + 1 ’Cer IV‘(NeuAc)Z,II’NeuAc-GgOse,Cer NeuAca2 + 8NeuAca2 + 3GalPI + 3GalNAcPI +4(NeuAca2 + 3)GalP1+4GlcPl+ 1 ‘Cer IV3NeuAc,II’(NeuAc),-GgOse,Cer NeuAca2+3GalPI -*3GalNAcPI+4(NeuAca2-+8NeuAcaZ+ 3)Gal,PI + 4 G l c P l + I’Cer I13(NeuAc),-GgOse,Cer GalPl+ 3GalNAcPl+4(NeuAca2 + 8NeuAca2- 8NeuAca2 + 3)GalPI + 4 G l c P l + I’Cer IV’(NeuAc)2,113(NeuAc),-GgOse,Cer NeuAcct2 + 8NeuAca2 + 3GalPI +3GalNAcPI -+4(NeuAca2 + 8NeuAca2 + 3)GalP1 +4GlcPI 1 ’Cer NeuAca2 3GalP 1 + 3GalNAcPI + 4(NeuAca2 + 8NeuAca2 -+ 8NeuAca2 + 3)GalP 1 -+ 4GlcP 1 + 1 ’Cer IV3NeuAc,II’(NeuAc),-GgOse,Cer IV’(NeuAc),,II‘(NeuAc),-GgOse,Cer NeuAca2 + 8NeuAca2 -* 8NeuAca2 3GalPI 43GalNAc,Pl+4(NeuAca2 + 8 NeuAca2+3)GalPl-+4GlcPl-+ 1‘Cer IV1(NeuAc),,II’(NeuAc),-GgOse,Cer NeuAca2 + 8NeuAca2 + 3GalP 1 +3GalNAcPI +4(NeuAca2 + 8NeuAca2 + 8 NeuAca2+3)GalPI +4Glc.P1+ I’Cer -+
-+
-+
--f
-+
-+
-
IUPAC-IUB (1977) Commission on Biochemical Nomenclature. The Nomenclature of Lipids. Lipids. 12: 455-468. Svennerholm, L. ( I 963) Chromatographic separation of human brain gangliosides. J. Neurochem., 10: 61 3-623. Svennerholm, L. (1980) Ganglioside designaltion. A h . Exp. Med. Biol.. 125: 11. (*) This ganglioside has often been designated GMI b. However, b is used in the Nomenclature to design a ganglioside of the ganglioseries with two sialic acids linked to the internal galactose (Svennerholm, 1963). (**)Terms within brackets ( ) represent branching point in the molecule. Abbreviations: Gal = galactose, Glc = glucose, GalNAc = N-acetylgalactosamine, GlcNAc = N-acetylglucosamine, Fuc = Fucose, NeuAc = N-acetylneuraminic acid, Cer = ceramide.
-x
I
TABLE 111
Ec
Designation and schematic structure of Lactoseries gangliosides of biological interest Designation
Schematic structure
Svennerholm (1980, 1988)
IUPAC-IUB (1 977)
3’-LM1 3’-isoLM1 6’-LM1 Fuc-3’-isoLM1 3‘,8‘-LD1 3’,6’-isoLD1
IV3NeuAc-nLcOse,Cer IV3NeuAc-LcOse,Cer IWNeu Ac-nLcOse,Cer IVINeuAc,l 1I4Fuc-LcOse,Cer IV>(NeuAc),-nLcOse,Cer
IV3NeuAc,lllhNeuAc-LcOse,Cer
NeuAca2+3Gal~1+4GIcNAcP1+3GalP1+4GlcPI + 1’Cer
NeuAca2+3GalPl+3GlcNAcPI -3GalPI +4GlcP1+ 1’Cer NeuAca2+6GalP1 -+4GlcNAcPI+3GalPI +4ClcPI + 1’Cer NeuAca2 -+ 3GalPI + 3(Fucal+4)GlcNAcPI + 3GalP +4GlcPI + I’Cer NeuAca2+8NeuAca2+3GalPI -t4GlcNAcP1-+3GalPI+4GlcP1 + 1’Cer NeuAca2-+ 3GaQ3I+ 3(NeuAca2+6)GIcNAcPl+ 3GalP1+4GlcPl+ 1’Cer
Svennerholm (1988) Immunological and tumoral aspects of gangliosides. In R.W. Ledeen, E.L. Hogan, G. Tettamanti, A.J. Yates and R.K. Yu (Eds), New Trends in Ganglioside Research, Fidia Research Series 14, Liviana Press, Padova, pp. 135-150. Abbreviations as in Table 11. TABLE IV Designation and schematic structure of glycosphingolipids related to gangliosides ~
~
~
~
Schematic structure
Designation Trivial
IUPAC-IUB (1 977)
Glucosylceramide Galactosylceramide Lactosylceramide (CDH) Trihexosylceramide (CTH) Globoside LA1 lactotetraosylceramidc (Paragloboside) isoLA1 isolactotetraosyl-ceramide LK1 Sulfoglucuronylneolactotetraosy lceramide (SGPG) HexLKl Sulfoglucuronyllactohexaosylceramide (SGLPG)
GlcCer GalCer LacCer GbOse,Cer GbOse,Cer nLcOse,Cer
GlcP I + 1 ’Cer GalPl +I‘Cer GalPl +4GlcPl+ 1‘Cer 1’Cer Gala1 +4GalP1+4Glc,PI GalNAc,PI - + 3 G a l a l+4GalPI +4GlcP1+ 1‘Cer GalPl+4GlcNAc~I+3GalP1 +4Glcj31 -+ I’Cer
isoLcOse,Cer
GalPl+3GlcNAcPI +3GalPI + 4 G l c P 1 4 1‘Cer 3-sulfateGlcUAP1 + 3GalPI +4GlcNAcP1+ 3 GalPl+4GlcP1+ 1’Cer
VIIGlcUA(3-sulfate)-nLc0se6Cer
3-sulfateGlcUA~l-+ 3Ga1,P I + 4GlcNAcPl -+ 3 GAP1 +4GlcNAcPI +3GalP1+4GlcP1+ 1‘Cer
IVZGlcUA(3-sulfate)-nLcOse,Cer
-+
Neolactotetraosylceramide was originally termed paragloboside when its structure was unknown. Para is derived from Greek and means beside, beyond wrong, irregular, and has been used in chemistry to denote a compound of unknown structure. When its structure has been elucidated I suggest that the name should be abandoned. 1 have suggested the name LKI and HexLKl for the two glucuronic acids containing acidic glycosphingolipids of the lactotetraose series since they occur in killer cells and have a Iactotetraose core structure.
Designation and Schematic Structure of Gangliosides and Allied Glycosphingolipids Lars Svennerholm Depurtment of Clinical Neuroscience, Section of Psychtarn and Neitrochemistn. University of Goteborg. Goteborg. Sweden
With gangliosides and other higher glycosphingolipids naming problems arise from the complexity of the carbohydrate moiety of these compounds. The systematic names of the oligosaccharides linked to the lipophilic portion, i.e. ceramide, are so cumbersome that they cannot be used for oral communication. This difficulty has been overcome by creating suitable trivial names for the parent oligosaccharides, with the prefixes ganglio-, globoand lacto- to which the number of monosaccharides in the oligosaccharide is indicated by the suffixes -triaose, -tetraose, etc. (IUPAC-IUB, 1977) (Table I). Klenk ( 1942) defined ganglioside as a complex glycosphingolipid containing sialic acid. When it was discovered that brain tissue contained several gangliosides (Svennerholm, 1955) with varying number of sialic acids we suggested the generic terms mono-, di-, and trisialogangliosides (Svennerholm and Raal, 1962) which were easily accepted. It was, however, much more difficult to agree about a common system of trivial names or symbols for the various gangliosides and most investigators preferred to introduce their own designation. For more than 10 years most ganglioside conferences devoted time for intense debates about the most appropriate designations of the various gangliosides. Today, the code system suggested by Svennerholm in 1963 and continuously extended (Svennerholm, 1980, 1988) is generally accepted for gangliosides of the ganglio series, while there is still no general agreement about the designation of gangliosides of the lactoseries. The designations suggested in 1963 were based on the findings that brain tissue contained four major gangliosides of the ganglio series with a tetraose chain of neutral sugars. They were designated to belong to the GI series where G stands for ganglio. The four gangliosides differed with regard to the number of sialic acids where M, D, and T stood for mono-, di-, and tri-sialyl groups. There were two disialogangliosides, GDla and GDlb, and that one which contained a disialylgroup at the internal galactose was designated b (Table 11). When gangliosides of the ganglio series with three sialic acids linked to the internal galactose were detected, they were designated to belong to the c series. When the biosynthesis of the gangliosides of the ganglio series has been finally settled it is evident that the designation of an a, b and c series predicted the crucial role of the sialytransferases in the ganglioside metabolism (Van Echten and Sandhoff, 1993). Gangliosides lacking the terminal galactose were given number 2 and when lacking the disaccharide galactosyl-N-acetylgalactosaminenumber 3. We have suggested the symbol cisGM 1 for the monosialogangliotetraosylceramide in which the sialyl group is attached to the terminal galactose. Some researchers have unfortunately already used the designation of G M l b for this ganglioside, but b is already used to designate gangliosides with a disialyl group attached to the internal galactose. The name G M l b ought to be abandoned. Differences in linkage (e.g. 1 + 4 versus 1 + 3) in otherwise identical sequences are in general indicated by ‘iso’ used as a prefix. We have used it in the nomenclature for the lactoseries gangliosides (Table 111). The designation of gangliosides of the lactoseries follows the principal for gangliosides of the ganglio series. We have used the term LMl for the sialyllactotetraosyl ceramide in which the terminal linkage is f3l -4, because it
XI1
occurs more abundantly in the nervous system and other organs under physiological conditions. Is0 LM1 is used for the ganglioside with a terminal f3l + 3 linkage. The designation paragloboside is still used for the lactotetraosylceramide. This term was given to the glycolipids when its chemical structure was unknown, but para means chemically related to or derived from (New Webster’s Dictionary, 1992) and it will be equally incorrect to continue to use the name paragloboside for lactotetraosylceramide as to use strandin (Folch-Pi, 1951) for ganglioside. Further, I have also suggested the short symbols LKl and HexLKl for the two glucuronic acid-containing glycosphingolipids of the lactotetraose series (L) since they occur in killer cells (K) and will react with the HNK-1 antibody (Table IV).
References Folch, J., Arsove, S. and Meath. J.A. (1951) Isolation of brain strandin, a new type of large molecule tissue component. J. B i d . Chem., 191: 819-830. IUPAC-IUB Commission on Biochemical Nomenclature (CBN) (1977) The Nomenclature of Lipids. Eur. J . Biochern., 79: 11-21, Klenk, E. (1942) Uber die Ganglioside, eine neue Gruppe von zucherhaltigen Gehirnlipoiden. Hoppe-Seyfer’sZ. fhysiof. Chem.. 273: 76-86. New Webster’s Dictionary and the Thesaurus of the English Language ( 1 992) Lexicon Publications Inc., Daubury, CT. Svennerholm, L. (1956) Composition of gangliosides from human brain. Nuture. 177: 524525. Svennerholm. L. (1963) Chromatographic separation of human brain gangliosides. J . Neurochem., 10: 613423. Svennerholm, L. (1980) Ganglioside designation. In: L. Svennerholm, P. Mandel, H. Dreyfus and P.F. Urban (Eds.) Structure and Function ofcangliosides. Adv. Exp. Med. Biol., Vol 125. Plenum Press, New York, pp. 11. Svennerholm, L. (1988) Immunological and tumoral aspects of gangliosides. In: R.W., Ledeen, E.L.. Hogan, G., Tettamanti, A.J., Yates and R.K., Yu. (Eds.) New Trends in Ganglioside Reseurch, Fidia Research Series, Vol 14. Liviana Press, Padova. pp. 135-150. Svennerholm, L. and Raal, A. (1961) Composition of brain gangliosides. Biochem. Biophvs. Actu, 53: 422424. Van Echten, G. and Sandhoff, K. (1993) Ganglioside metabolism: enzymology, topology and regulation, J. Biol. Chem., 268: 5341-5344.
TABLE I Names and abbreviations of neutral glycosphingolipids Structure GalNAcPl+ 4GalP 1 4GlcCer 3GalNAcP 1 + 4GalP I + 4GIcCer -+
GalP I
-+
GalNAcP 1
-
Gala 1 + 4GalP 1 -+ 4GlcCer 3Gala 1 -+ 4GalP 1 -+ 4GlcCer
GlcNAcP 1 + 3GalP 1 -+ 4GlcCer GalP 1 -+ 4GLcNAcP 1 + 3GalP 1 4GlcCer GalP 1 3GlcNAcP 1 + 3GalP I 4GlcCer -+
-+
-+
Trivial name of oligosaccharide
Designation of glycosphingolipid
Gangliotriaose Gangliotetraose
GgOse,Cer GgOse,Cer
Globotriaose Globotetraose
GbOse,Cer GbOse,Cer
Lactotriaose Lactotetraose isoLactotetraose
LcOse,Cer LcOse,Cer isoLcOse,Cer
TABLE I1 Designation and schematic structure of ganglioseries gangliosides of biological interest. Schematic structure
Designation -
Svennerholm IUPAC-IUB (1977) (1963, 1980) GM4 GM3 GM2 GM 1 cis GMI ( * ) FUC-GM1 GD3 GD2 GDla GDIb Fuc-GD 1b GT3 GTla GTlb GTI c GQlb GQlc GPlb GPlc
I’NeuAc-GalCer II’Neu Ac-LacCer
NeuAca2 + 3GalP 1 + 1 ‘Cer NeuAca2 + 3GalPI +4Glc@I + 1’Cer II'Neu Ac-GgOse,Cer ~I+ GalNAcPl+4(NeuAca2 + 3) ~ “ ~ G a l ~ l + 4 G l cI‘Cer II’NeuAc-GgOse,Cer Gal,PI +3GalNAcPI +4(NeuAca2-+3)GalPI +4GlcPI + I’Cer WNeuAc-GgOse,Ger NeuAca2+3GalPI +3GalNAcPI -4GalPI -4GlcPI + I‘Cer IV’Fuc,II’NeuAc-GgOse,Cer Fucal + 2GalP 1 + 3GalNAcP I + 4(NeuAca2 3)GalPI +4GlcPI + 1‘Cer II’(NeuAc)Z-LacCer NeuAca2 + 8NeuAca2 + 3GalPl+ 4GlcPI + 1‘Cer GalNAcP 1 4(Neua2 + 8NeuAca2 + 3)GalP1 +4GlcP 1 + 1‘Cer I13(NeuAc)2-GgOse,Cer IV’NeuAc,II’NeuAc-GgOse,Cer NeuAca2 + 3GalP 1 + 3GalNAcP 1 +4(NeuAca2 + 3)GalP I +4GlcP 1 + 1 ‘Cer GalPl+ 3GalNAcPI +4(NeuAca2 + 8NeuAca2 3)GalPI +4GlcPI + 1‘Cer II’(NeuAc),-GgOse,Cer IV1Fuc,11’(NeuAc)2-GgOse,Cer I’Cer Fucal+2GalPI +3GalNAc~1+4(NeuAca2+8NeuAca2+3)Gal~l-+4Glc~l+ II’(NeuAc),-LacCer NeuAca2 + 8NeuAca2 + 8NeuAca2 + 3GalP 1 +4GlcPI + 1 ’Cer IV‘(NeuAc)Z,II’NeuAc-GgOse,Cer NeuAca2 + 8NeuAca2 + 3GalPI + 3GalNAcPI +4(NeuAca2 + 3)GalP1+4GlcPl+ 1 ‘Cer IV3NeuAc,II’(NeuAc),-GgOse,Cer NeuAca2+3GalPI -*3GalNAcPI+4(NeuAca2-+8NeuAcaZ+ 3)Gal,PI + 4 G l c P l + I’Cer I13(NeuAc),-GgOse,Cer GalPl+ 3GalNAcPl+4(NeuAca2 + 8NeuAca2- 8NeuAca2 + 3)GalPI + 4 G l c P l + I’Cer IV’(NeuAc)2,113(NeuAc),-GgOse,Cer NeuAcct2 + 8NeuAca2 + 3GalPI +3GalNAcPI -+4(NeuAca2 + 8NeuAca2 + 3)GalP1 +4GlcPI 1 ’Cer NeuAca2 3GalP 1 + 3GalNAcPI + 4(NeuAca2 + 8NeuAca2 -+ 8NeuAca2 + 3)GalP 1 -+ 4GlcP 1 + 1 ’Cer IV3NeuAc,II’(NeuAc),-GgOse,Cer IV’(NeuAc),,II‘(NeuAc),-GgOse,Cer NeuAca2 + 8NeuAca2 -* 8NeuAca2 3GalPI 43GalNAc,Pl+4(NeuAca2 + 8 NeuAca2+3)GalPl-+4GlcPl-+ 1‘Cer IV1(NeuAc),,II’(NeuAc),-GgOse,Cer NeuAca2 + 8NeuAca2 + 3GalP 1 +3GalNAcPI +4(NeuAca2 + 8NeuAca2 + 8 NeuAca2+3)GalPI +4Glc.P1+ I’Cer -+
-+
-+
--f
-+
-+
-
IUPAC-IUB (1977) Commission on Biochemical Nomenclature. The Nomenclature of Lipids. Lipids. 12: 455-468. Svennerholm, L. ( I 963) Chromatographic separation of human brain gangliosides. J. Neurochem., 10: 61 3-623. Svennerholm, L. (1980) Ganglioside designaltion. A h . Exp. Med. Biol.. 125: 11. (*) This ganglioside has often been designated GMI b. However, b is used in the Nomenclature to design a ganglioside of the ganglioseries with two sialic acids linked to the internal galactose (Svennerholm, 1963). (**)Terms within brackets ( ) represent branching point in the molecule. Abbreviations: Gal = galactose, Glc = glucose, GalNAc = N-acetylgalactosamine, GlcNAc = N-acetylglucosamine, Fuc = Fucose, NeuAc = N-acetylneuraminic acid, Cer = ceramide.
-x
I
TABLE 111
Ec
Designation and schematic structure of Lactoseries gangliosides of biological interest Designation
Schematic structure
Svennerholm (1980, 1988)
IUPAC-IUB (1 977)
3’-LM1 3’-isoLM1 6’-LM1 Fuc-3’-isoLM1 3‘,8‘-LD1 3’,6’-isoLD1
IV3NeuAc-nLcOse,Cer IV3NeuAc-LcOse,Cer IWNeu Ac-nLcOse,Cer IVINeuAc,l 1I4Fuc-LcOse,Cer IV>(NeuAc),-nLcOse,Cer
IV3NeuAc,lllhNeuAc-LcOse,Cer
NeuAca2+3Gal~1+4GIcNAcP1+3GalP1+4GlcPI + 1’Cer
NeuAca2+3GalPl+3GlcNAcPI -3GalPI +4GlcP1+ 1’Cer NeuAca2+6GalP1 -+4GlcNAcPI+3GalPI +4ClcPI + 1’Cer NeuAca2 -+ 3GalPI + 3(Fucal+4)GlcNAcPI + 3GalP +4GlcPI + I’Cer NeuAca2+8NeuAca2+3GalPI -t4GlcNAcP1-+3GalPI+4GlcP1 + 1’Cer NeuAca2-+ 3GaQ3I+ 3(NeuAca2+6)GIcNAcPl+ 3GalP1+4GlcPl+ 1’Cer
Svennerholm (1988) Immunological and tumoral aspects of gangliosides. In R.W. Ledeen, E.L. Hogan, G. Tettamanti, A.J. Yates and R.K. Yu (Eds), New Trends in Ganglioside Research, Fidia Research Series 14, Liviana Press, Padova, pp. 135-150. Abbreviations as in Table 11. TABLE IV Designation and schematic structure of glycosphingolipids related to gangliosides ~
~
~
~
Schematic structure
Designation Trivial
IUPAC-IUB (1 977)
Glucosylceramide Galactosylceramide Lactosylceramide (CDH) Trihexosylceramide (CTH) Globoside LA1 lactotetraosylceramidc (Paragloboside) isoLA1 isolactotetraosyl-ceramide LK1 Sulfoglucuronylneolactotetraosy lceramide (SGPG) HexLKl Sulfoglucuronyllactohexaosylceramide (SGLPG)
GlcCer GalCer LacCer GbOse,Cer GbOse,Cer nLcOse,Cer
GlcP I + 1 ’Cer GalPl +I‘Cer GalPl +4GlcPl+ 1‘Cer 1’Cer Gala1 +4GalP1+4Glc,PI GalNAc,PI - + 3 G a l a l+4GalPI +4GlcP1+ 1‘Cer GalPl+4GlcNAc~I+3GalP1 +4Glcj31 -+ I’Cer
isoLcOse,Cer
GalPl+3GlcNAcPI +3GalPI + 4 G l c P 1 4 1‘Cer 3-sulfateGlcUAP1 + 3GalPI +4GlcNAcP1+ 3 GalPl+4GlcP1+ 1’Cer
VIIGlcUA(3-sulfate)-nLc0se6Cer
3-sulfateGlcUA~l-+ 3Ga1,P I + 4GlcNAcPl -+ 3 GAP1 +4GlcNAcPI +3GalP1+4GlcP1+ 1‘Cer
IVZGlcUA(3-sulfate)-nLcOse,Cer
-+
Neolactotetraosylceramide was originally termed paragloboside when its structure was unknown. Para is derived from Greek and means beside, beyond wrong, irregular, and has been used in chemistry to denote a compound of unknown structure. When its structure has been elucidated I suggest that the name should be abandoned. 1 have suggested the name LKI and HexLKl for the two glucuronic acids containing acidic glycosphingolipids of the lactotetraose series since they occur in killer cells and have a Iactotetraose core structure.