Syntheses of glycosylamides as glycolipid analogs

被引:29
作者
Lockhoff, O [1 ]
Stadler, P [1 ]
机构
[1] Bayer AG, Cent Res, D-51368 Leverkusen, Germany
关键词
glycolipid analog; glycosylamine; glycosylamide; anomerisation; immunomodulator;
D O I
10.1016/S0008-6215(98)00278-X
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In search of a simple synthetic access to analogs of naturally occurring glycolipids, glycosylamides have been synthesised in a two-step procedure from unprotected sugars, long-chain amines, and fatty acids. The N-glycosylation proceeded stereospecifically yielding crystalline beta-glycopyranosylamines. C-13 NMR spectroscopy of the glycosylamines in organic solvents revealed partial anomerisation, leading to alpha-glycosylamines and in part to corresponding N-furanosides. Selective N-acylation of either pure beta-glycosylamines or anomeric mixtures thereof with activated fatty acid led to formation of beta-glycosylamides exclusively. As evidenced by NMR spectroscopy, the glycosylamides exhibited rotameric isomerism. The glycosylamides were found to be strong stimulators of the specific immune response against antigens. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码:13 / 24
页数:12
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