SYNTHESIS OF THE METHYL GLYCOSIDES OF A TRISACCHARIDE AND A TETRASACCHARIDE RELATED TO HEPARIN AND HEPARAN-SULFATE

被引:38
作者
NILSSON, M
SVAHN, CM
WESTMAN, J
机构
[1] Organic Chemistry, Kabi Pharmacia AB, S-112 87 Stockholm, Sweden
关键词
D O I
10.1016/0008-6215(93)84030-A
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
The methyl glycoside of a tetrasaccharide isolated from heparin, methyl O-(alpha-L-idopyranosyluronic acid)-(1 --> 4)-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-(1 --> 4)-O-(beta-D-glucopyranosyluronic acid)-(1 --> 3)-O-beta-D-galactopyranoside disodium salt and a trisaccharide derivative thereof, methyl O-(alpha-L-idopyranosyluronic acid)-(1 --> 4)-O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-(1 --> 4)-O-beta-D-glucopyranosyluronic acid disodium salt, were synthesized using a block-type strategy. A suitable protected disaccharide block of iduronic acid and glucosamine (IdoA-GlcN) was used as a key intermediate for the syntheses and was glycosidated with a protected galactose derivative and a disaccharide block of glucuronic acid and galactose (GlcA-Gal) to give tri- and tetra-saccharide derivatives, respectively. Deprotection gave the target compounds.
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页码:161 / 172
页数:12
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