New modified single chained glycolipids. Part 1: synthesis of deoxy and partially O-methylated glycolipids with or without a sulfur containing spacer.
A way to synthesize neoglycolipids with high yields and anomeric purity is described. Starting point of the synthesis strategy is the glycosylation of allyl alcohol with definite steric orientation. Introduction of the hydrophobic moiety was achieved by photoaddition of n-hexadecanethiol and 3-mercaptopropionic acid followed by amidation with n-hexadecylamine, respectively. In order to investigate the influence of different carbohydrate headgroups in the physicochemical behavior of the general glycolipid, especially the orientation of the alkyl chain, a range of neoglycolipids was synthesized. Beside the differences in the configuration between unfunctionalized glycopyranoses like D-glucose, D-galactose and D-mannose, a number of deoxy and partially O-methylated sugar derivatives was prepared. The divergences concerning the different carbohydrate headgroups and the hydrophobic moiety, respectively, can be compared to relatively simple structured glycolipids with hexadecyl residue and without spacer function.
Schmidt
M
M
Institute of Pharmaceutical Chemistry, Martin-Luther-University, Wolfgang-Langenbeck-Strasse 4, D-06120 Halle/Saale, Germany.
Chatterjee
S K
SK
Dobner
B
B
Nuhn
P
P
D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D008745:Methylation; D015394:Molecular Structure; D013455:Sulfur / Q000737:chemistry
D006017:Glycolipids; D013455:Sulfur