Chemoenzymatic synthesis of ganglioside GM4 analogs as potential immunosuppressive agents 1

Article abstract of DOI:10.1080/07328309908543992

An efficient, chemoenzymatic synthesis of ganglioside GM4 analogs having a potent immunosuppressive activity is described. One-step and highly regioselective 6-O-acetylation of long-chain alkyl, 2-(trimethysilyl)ethyl and phenyl 1-thio β-D-galactopyranosides was performed by using vinyl acetate and lipase PS. The resulting 6-O-acetates (70-93%) were sialylated with methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonu lopyranosid)onate promoted by N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). The 2-(trimethylsilyl)ethyl glycoside derivative was converted to the imidate which was then coupled with dodecan-1-ol, hexadecan-1-ol, and 2-(tetradecyl)hexadecan-1-ol, respectively, to give the protected GM4 derivatives (90-96%). O-Deacylation and saponification of the methyl ester gave the target ganglioside GM4 analogs in high yields.

Full text of DOI:10.1080/07328309908543992

Journal of Carbohydrate Chemistry
ISSN: 0732-8303 (Print) 1532-2327 (Online) Journal homepage: http://www.tandfonline.com/loi/lcar20
Chemoenzymatic Synthesis of Ganglioside Gm4
Analogs as Potential Immunosuppressive Agents
Xiaodong Zhang , Tomohide Kamiya , Nobumasa Otsubo , Hideharu Ishida &
Makoto Kiso
To cite this article: Xiaodong Zhang , Tomohide Kamiya , Nobumasa Otsubo , Hideharu
Ishida & Makoto Kiso (1999) Chemoenzymatic Synthesis of Ganglioside Gm4 Analogs as
Potential Immunosuppressive Agents, Journal of Carbohydrate Chemistry, 18:2, 225-239, DOI:
10.1080/07328309908543992
To link to this article: http://dx.doi.org/10.1080/07328309908543992
Published online: 27 Feb 2008.
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Date: 01 December 2015, At: 07:26