A SIMPLE SYNTHESIS OF OCTYL 3,6-DI-O-(ALPHA-D-MANNOPYRANOSYL)-BETA-D-MANNOPYRANOSIDE AND ITS USE AS AN ACCEPTOR FOR THE ASSAY OF N-ACETYLGLUCOSAMINYLTRANSFERASE-I ACTIVITY

被引：48

作者：

KAUR, KJ ^{[1
]}

HINDSGAUL, O ^{[1
]}

机构：

[1] UNIV ALBERTA,DEPT CHEM,EDMONTON T6G 2G2,ALBERTA,CANADA

来源：

GLYCOCONJUGATE JOURNAL | 1991年 / 8卷 / 02期

关键词：

N-ACETYLGLUCOSAMINYLTRANSFERASE-I; GLYCOSYLTRANSFERASE ASSAY; CORE-TRIMANNOSIDE; OLIGOSACCHARIDE SYNTHESIS;

D O I：

10.1007/BF00731017

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：

A simple synthesis of octyl 3,6-di-O-(alpha-D-mannopyranosyl)-beta-D-mannopyranoside is described. The key features of the synthetic scheme are the formation of the beta-mannosidic linkage by 1-O-alkylation of 2,3,4,6-tetra-O-acetyl-alpha,beta-D-mannopyranose with octyl iodide and glycosylation of unprotected octyl beta-D-mannopyranoside using limiting acetobromomannose. The trisaccharide is shown to be an acceptor for N-acetylglucosaminyltransferase-I with a K(M) of 585-mu-M.

引用

页码：90 / 94

页数：5

共 28 条

[11] PSEUDO-SUGARS .28. SYNTHESIS OF 2-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-5A-CARBA-ALPHA-D-MANNOPYRANOSE, AND 5A-CARBA-2-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSE AND 5A-CARBA-3,6-DI-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSES
OGAWA, S
NISHI, K
CARBOHYDRATE RESEARCH, 1992, 229 (01) : 117 - 129
[12] Synthesis of a tri- and a tetradeoxy analogue of methyl 3,6-di-O-α-D-mannopyranosyl-α-D-mannopyranoside for investigation of the binding site of various plant lectins
Oscarson, S
Svahnberg, P
CARBOHYDRATE RESEARCH, 1998, 309 (02) : 207 - 212
[13] SYNTHESIS OF THE METHYL, 1-OCTYL, AND PARA-TRIFLUOROACETAMIDOPHENYLETHYL ALPHA-GLYCOSIDES OF 3,6-DI-O-(ALPHA-D-GALACTOPYRANOSYL)-D-GLUCOPYRANOSE AND AN ACYCLIC ANALOG THEREOF
NORBERG, T
WALDING, M
WESTMAN, E
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (02) : 283 - 292
[14] SYNTHESIS OF OCTYL 2-O-ALPHA-D-MANNOPYRANOSYL-ALPHA-D-MANNOPYRANOSIDE, ITS 6'-PHOSPHATE AND THE CORRESPONDING MONOMETHYL PHOSPHODIESTER - INTERMEDIATE STRUCTURES IN THE BIOSYNTHESIS OF N-LINKED OLIGOSACCHARIDES IN DICTYOSTELIUM-DISCOIDIUM
HALLGREN, C
HINDSGAUL, O
CARBOHYDRATE RESEARCH, 1994, 260 (01) : 63 - 71
[15] Synthesis of 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->2)-alpha-D-mannopyranosyl(1->6)-beta-D-mannopyranosyl-(1->4)-2-acetamido-2-deoxy-D-glucopyranose. Acceptor-substrate recognition by N-acetylglucosaminyltransferase-V (GnT-V)
Khan, SH
Matta, KL
CARBOHYDRATE RESEARCH, 1995, 278 (02) : 351 - 362
[16] SYNTHESIS OF A TETRASACCHARIDE ACCEPTOR FOR USE IN THE ASSAY OF UDP-GLCPNAC - BETA-D-GALP-(1-]4)-BETA-D-GLCPNAC (GLCNAC TO GAL) BETA(1-]3)-N-ACETYLGLUCOSAMINYLTRANSFERASE ACTIVITY AND THE PENTASACCHARIDE PRODUCT THAT WOULD BE FORMED BY ITS ENZYMATIC GLYCOSYLATION
SRIVASTAVA, G
HINDSGAUL, O
CARBOHYDRATE RESEARCH, 1992, 224 : 83 - 93
[17] SYNTHESIS OF O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]2)-O-ALPHA-D-MANNOPYRANOSYL-(1-]6)-O-BETA-D-GLUCOPYRANOSYL-(1-]4)-2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE - A POTENTIAL ACCEPTOR-SUBSTRATE FOR N-ACETYLGLUCOSAMINYLTRANSFERASE-V (GNT-V)
KHAN, SH
MATTA, KL
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1993, 12 (03) : 335 - 348
[18] Synthesis of alpha-D-Glcp-(1 -> 2)-alpha-D-Glcp-(1->3)-alpha-D-Glcp-O-(CH2)(8)COOCH3 for use in the assay of alpha-glucosidase I activity
Scaman, CH
Hindsgaul, O
Palcic, MM
Srivastava, OP
CARBOHYDRATE RESEARCH, 1996, 296 : 203 - 213
[19] SYNTHESIS OF BETA-D-GLCPNAC-(1-]2)-5A-CARBA-ALPHA-D-MANP-(1-]6)-BETA-D-GLCP-O(CH2)(7)CH3 - A REACTIVE ACCEPTOR ANALOG FOR N-ACETYLGLUCOSAMINYLTRANSFERASE-V
OGAWA, S
FURUYA, T
TSUNODA, H
HINDSGAUL, O
STANGIER, K
PALCIC, MM
CARBOHYDRATE RESEARCH, 1995, 271 (02) : 197 - 205
[20] SYNTHETIC STUDIES IN CARBOHYDRATES .67. SYNTHESIS OF 4-NITROPHENYL O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLU-COPYRANOSYL)-(1-]2)-O-(4-O-METHYL-ALPHA-D-MANNOPYRANOSYL)-(1-]6)-BETA-D-GLUCOPYRANOSIDE - A POTENTIAL SPECIFIC ACCEPTOR-SUBSTRATE FOR N-ACETYLGLUCOSAMINYLTRANSFERASE-V (GNT V)
KHAN, SH
ABBAS, SA
MATTA, KL
CARBOHYDRATE RESEARCH, 1990, 205 : 385 - 397

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