Synthetic studies on sialoglycoconjugates 89: Synthesis of ganglioside GM3 and KDN-GM3 containing different carbon-chain length fatty acyl groups at the ceramide residue

Article abstract of DOI:10.1080/07328309608005680

Ganglioside GM₃ and KDN-ganglioside GM₃, containing hexanoyl, decanoyl, and hexadecanoyl groups at the ceramide moiety have been synthesized. Selective reduction of the azido group in O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2- nonulopyranosylonate)-(2→3)-O-(2,4-di-O-acetyl-6-O-benzoyl-β-D- galactopyranosyl)-(1→4)-O-(3-O-acetyl-2,6-di-O-benzoyl-β-D- glucopyranosyl)-(1→1)-(2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (1) and O-(methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2- nonulopyranosylonate)-(2→3)-O-(2,4-di-O-acetyl-6-O-benzoyl-β-D- galactopyranosyl)-(1→4)-O-(3-O-acetyl-2,6-di-O-benzoyl-β-D- glucopyranosyl)-(1→1)-(2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (2), coupling with hexanoic, decanoic, and hexadecanoic acids, O-deacylation, and de-esterification gave the title gangliosides GM₃ (11～13) and KDN-GM₃ (14～16) in good yields. On the other hand, O-deacylation of 1 and subsequent de-esterification gave 2-azido-sphingosine containing-GM₃ analogue 17, which was converted into lyso-GM₃, in which no fatty acyl group was substituted at the sphingosine residue, by selective reduction of the azido group.

Full text of DOI:10.1080/07328309608005680

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Synthetic Studies on
Sialoglycoconjugates 89: Synthesis of
Ganglioside GM3 and KDN-GM3 Containing
Different Carbon-Chain Length Fatty Acyl
Groups at the Ceramide Residue
Akira Hasegawa a , Naomi Suzuki a , Fumitaka Kozawa a , Hideharu
Ishida a & Makoto Kiso a
a Department of Applied Bioorganic Chemistry , Gifu University ,
Gifu, 501-11, Japan
Published online: 22 Aug 2006.
To cite this article: Akira Hasegawa , Naomi Suzuki , Fumitaka Kozawa , Hideharu Ishida & Makoto
Kiso (1996) Synthetic Studies on Sialoglycoconjugates 89: Synthesis of Ganglioside GM3 and KDN-GM3
Containing Different Carbon-Chain Length Fatty Acyl Groups at the Ceramide Residue, Journal of
Carbohydrate Chemistry, 15:5, 639-648, DOI: 10.1080/07328309608005680
To link to this article: http://dx.doi.org/10.1080/07328309608005680
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