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
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
收藏
页码:29 / 42
页数:14
相关论文
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