SYNTHESIS OF 4-NITROPHENYL O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-ALPHA-2)-O-(6-O-METHYL-ALPHA-D-MANNOPYRANOSYL)-(1-ALPHA-6)-BETA-D-GLUCOPYRANOSIDE AND ITS 4',6'-DI-O-METHYL ANALOG - POTENTIAL INHIBITORS OF N-ACETYLGLUCOSAMINYL-TRANSFERASE-V (GNT-V)

被引：13

作者：

KHAN, SH ^{[1
]}

MATTA, KL ^{[1
]}

机构：

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

来源：

CARBOHYDRATE RESEARCH | 1993年 / 243卷 / 01期

关键词：

D O I：

10.1016/0008-6215(93)84079-L

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：

O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1 --> 2)-3,4-di-O-acetyl-6-O-methyl-alpha-D-mannopyranosyl bromide and O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1 --> 2)-3-O-acetyl-4,6-di-O-methyl-alpha-D-mannopyranosyl bromide were each condensed with 4-nitrophenyl 2,3-di-O-acetyl-beta-D-glucopyranoside, and the products were deprotected to yield, respectively, beta-D-Glc p NAc-(1 --> 2)-6-O-Me-alpha-D-Man p-(1 --> 6)-beta-D-Glc p and beta-D-Glc p NAc-(1 --> 2)-4,6-di-O-Me-alpha-D-Man p-(1 --> 6)-beta-D-Glc p, as their 4-nitrophenyl glycosides. These trisaccharides are expected to function as inhibitors for N-acetylglucosaminyltransferase V.

引用

页码：29 / 42

页数：14

共 26 条

[1] SYNTHETIC STUDIES IN CARBOHYDRATES .51. SYNTHESIS OF 2-ACETAMIDO-2-DEOXY-4-O-(2-O-METHYL-BETA-D-GALACTOPYRANOSYL)-D-GLUCOPYRANOSE (N-ACETYL-2'-O-METHYLLACTOSAMINE) [J].

ABBAS, SA ;

PISKORZ, CF ;

MATTA, KL .

CARBOHYDRATE RESEARCH, 1987, 167 :131-141

[2] COMPARISON OF N-ACETYLGLUCOSAMINYLTRANSFERASE-V ACTIVITIES IN ROUS SARCOMA-TRANSFORMED BABY HAMSTER-KIDNEY (RS-BHK) AND BHK CELLS [J].

ARANGO, J ;

PIERCE, M .

JOURNAL OF CELLULAR BIOCHEMISTRY, 1988, 37 (02) :225-231

[3] Acetone derivatives of methylglycosides. [J].

Ault, RG ;

Haworth, WN ;

Hirst, EL .

JOURNAL OF THE CHEMICAL SOCIETY, 1935, :1012-1020

[4] CONTROL OF GLYCOPROTEIN-SYNTHESIS - CHARACTERIZATION OF (1-]4)-N-ACETYL-BETA-D-GLUCOSAMINYLTRANSFERASES ACTING ON THE ALPHA-D-(1-]3)-LINKED AND ALPHA-D-(1-]6)-LINKED ARMS OF N-LINKED OLIGOSACCHARIDES [J].

BROCKHAUSEN, I ;

MOLLER, G ;

YANG, JM ;

KHAN, SH ;

MATTA, KL ;

PAULSEN, H ;

GREY, AA ;

SHAH, RN ;

SCHACHTER, H .

CARBOHYDRATE RESEARCH, 1992, 236 :281-299

[5]

BROCKHAUSEN I, UNPUB

[6]

CUMMINGS RD, 1982, J BIOL CHEM, V257, P13421

[7]

DENNIS JW, 1988, CANCER SURV, V7, P573

[8]

DENNIS JW, 1989, ONCOGENE, V4, P853

[9]

DENNIS JW, 1989, CANCER RES, V49, P945

[10] BETA-1-6 BRANCHING OF ASN-LINKED OLIGOSACCHARIDES IS DIRECTLY ASSOCIATED WITH METASTASIS [J].

DENNIS, JW ;

LAFERTE, S ;

WAGHORNE, C ;

BREITMAN, ML ;

KERBEL, RS .

SCIENCE, 1987, 236 (4801) :582-585

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