SYNTHESIS OF TETRASACCHARIDE ANALOGS OF THE N-GLYCAN SUBSTRATE OF BETA-(1-]2)-N-ACETYLGLUCOSAMINYLTRANSFERASE-II USING TRISACCHARIDE PRECURSORS AND RECOMBINANT BETA-(1-]2)-N-ACETYLGLUCOSAMINYLTRANSFERASE-I

被引：20

作者：

RECK, F

SPRINGER, M

PAULSEN, H

BROCKHAUSEN, I

SARKAR, M

SCHACHTER, H

机构：

[1] HOSP SICK CHILDREN, RES INST, TORONTO M5G 1X8, ON, CANADA

[2] UNIV HAMBURG, INST ORGAN CHEM, D-20146 HAMBURG, GERMANY

[3] UNIV TORONTO, DEPT BIOCHEM, TORONTO M5S 1A8, ON, CANADA

来源：

CARBOHYDRATE RESEARCH | 1994年 / 259卷 / 01期

基金：

英国医学研究理事会;

关键词：

D O I：

10.1016/0008-6215(94)84200-0

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：

Recombinant rabbit UDP-GlcNAc:alpha-Man-(1 --> 3R) beta-(1 --> 2)-N-acetylglucosaminyltransferase I (EC 2.4.1.101, GlcNAc-T I) produced in the Sf9 insect cell/baculovirus expression system has been used to convert compounds of the form 3-R-alpha-Man(1 --> 6)(alpha-Man(1 --> 3))beta-Man-O-octyl to 3-R-alpha-Man(1 --> 6)(beta-GlcNAc(1 --> 2)alpha-Man(1 --> 3))beta-Man-O-octyl where R is OH (14), O-methyl (17), O-pentyl (18), O-(4,4-azo)pentyl (19), O-(5-iodoacetamido)pentyl (20) and O-(5-amino)pentyl (21); 2-deoxy-alpha-Man(1 --> 6)(beta-GlcNAc(1 --> 2)alpha-Man(1 --> 3))beta-Man-O-octyl (16), 4-O-methyl-alpha-Man(1 --> 6)(beta-GlcNAc(1 --> 2)alpha-Man(1 --> 3))beta-Man-O-octyl (22), 6-O-methyl-alpha-Man(1 --> 6)(beta beta-GlcNAc(1 --> 2)alpha-Man(1 --> 3))beta-Man-O-octyl (23) and alpha-Man(1 --> 6)[beta-GlcNAc(1 --> 2)(4-O-methyl)alpha-Man(1 --> 3)]beta-Man-O-octyl (15) were also synthesized by this procedure. The yields ranged from 80 to 99%. Products were characterized by high resolution H-1 and C-13 nuclear magnetic resonance spectroscopy and fast atom bombardment mass spectrometry. Compounds 14, 15, 17, 22, and 23 are excellent substrates for UDP-GlcNAc:alpha-Man(1 --> 6R) beta-(1 --> 2)-N-acetylglucosaminyltransferase II and the other compounds are inhibitors of this enzyme.

引用

页码：93 / 101

页数：9

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