SYNTHETIC MUCIN FRAGMENTS - SYNTHESIS OF O-SULFO AND O-METHYL DERIVATIVES OF ALLYL O-(BETA-D-GALACTOPYRANOSYL)-(1-]3)-2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE AS POTENTIAL COMPOUNDS FOR SULFOTRANSFERASES

被引：4

作者：

JAIN, RK ^{[1
]}

PISKORZ, CF ^{[1
]}

MATTA, KL ^{[1
]}

机构：

[1] ROSWELL PK CANC INST,DEPT GYNECOL ONCOL,BUFFALO,NY 14263

来源：

CARBOHYDRATE RESEARCH | 1995年 / 275卷 / 02期

关键词：

MUCIN FRAGMENTS; SULFOTRANSFERASES; C-13; NMR; FAB MASS SPECTROSCOPY;

D O I：

10.1016/0008-6215(95)00162-M

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：

Allyl 2-acetamido-4,6-O-(4-methoxybenzylidene)-2-deoxy-alpha-D-galactopyranoside (1) was condensed with either 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide (2) or 2,3,4-tri-O-benzoyl-6-O-bromoacetyl-alpha-D-galactopyranosyl bromide (14) in the presence of mercuric cyanide. Selective substitution with methyl, sulfo or both at desired positions, followed by the removal of protecting groups, afforded allyl O-(beta-D-galactopyranosyl)-(1 --> 3)-2-acetamido-2-deoxy-6-O-methyl-alpha-D-galactopyranoside (5), allyl O-(6-O-sulfo-beta-D-galactopyranosyl sodium salt)-(1 --> 3)-2-acetamido-2-deoxy-6-O-methyl-alpha-D-galactopyranoside (10), allyl O-(beta-D-galactopyranosyl)-(1 -> 3)-2-acetamido-2-deoxy-6-O-sulfo-alpha-D-galactopyranoside sodium salt (13), allyl O-(6-O-sulfo-beta-D-galactopyranosyl sodium salt)-(1 --> 3)-2-acetamido-2-deoxy-alpha-D-galactopyranoside (17) and allyl O-(3-O-sulfo-beta-D-galactopyranosyl sodium salt)-(1 --> 3)-2-acetamido-2-deoxy-alpha-D-galactopyranoside (22). The structures of compounds 5, 10, 13, 17 and 22 were established by C-13 NMR and FAB mass spectroscopy.

引用

页码：231 / 243

页数：13

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