A moenomycin-type structural analogue of lipid II some possible mechanisms of the mode of action of transglycosylase inhibitors can be discarded

被引:15
作者
Kosmol, R
Hennig, L
Welzel, P
Findeisen, M
Muller, D
Markus, A
vanHeijenoort, J
机构
[1] UNIV LEIPZIG,INST ORGAN CHEM,D-04103 LEIPZIG,GERMANY
[2] UNIV LEIPZIG,INST ANALYT CHEM,D-04103 LEIPZIG,GERMANY
[3] RUHR UNIV BOCHUM,FAK CHEM & MINERAL,D-4630 BOCHUM,GERMANY
[4] HOECHST AG,D-6230 FRANKFURT,GERMANY
[5] UNIV PARIS 11,ORSAY,FRANCE
来源
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1997年 / 339卷 / 04期
关键词
D O I
10.1002/prac.19973390162
中图分类号
O69 [应用化学];
学科分类号
081704 [应用化学];
摘要
The transglycosylation step in the peptidoglycan biosynthesis belongs to the general class of glycosyltransferase-catalyzed reactions. The structural analogue 2 of moenomycin A has been synthesized and has been found to be antibiotically inactive. The assumption that moenomycin-type transglycosylase inhibitors such as 1 bind at the donor site of the enzyme and that their mode of action is the result of the high stability of the sugar --> phosphate bond seems to be ruled out by the present results.
引用
收藏
页码:340 / 358
页数:19
相关论文
共 65 条
[1]
OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].
BAL, BS ;
CHILDERS, WE ;
PINNICK, HW .
TETRAHEDRON, 1981, 37 (11) :2091-2096
[2]
DIMERIZATION AND MEMBRANE ANCHORS IN EXTRACELLULAR TARGETING OF VANCOMYCIN GROUP ANTIBIOTICS [J].
BEAUREGARD, DA ;
WILLIAMS, DH ;
GWYNN, MN ;
KNOWLES, DJC .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1995, 39 (03) :781-785
[3]
SHORT-CHAIN DOLICHOLS OF DEFINED CHAIN-LENGTH AS COFACTORS IN REACTIONS OF THE MICROSOMAL DOLICHYL-PHOSPHATE CYCLE AND TRANSGLYCOSYLATIONS [J].
BERENDES, R ;
JAENICKE, L .
BIOLOGICAL CHEMISTRY HOPPE-SEYLER, 1992, 373 (01) :35-42
[4]
HYDROGENOLYSIS OF CARBOHYDRATE ACETALS KETALS AND CYCLIC ORTHOESTERS WITH LITHIUM ALUMINIUM YDRIDE - ALUMINIUM TRICHLORIDE [J].
BHATTACH.SS ;
GORIN, PAJ .
CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (07) :1195-&
[5]
THE USE OF 2-DEOXY-2-TRICHLOROACETAMIDO-D-GLUCOPYRANOSE DERIVATIVES IN SYNTHESES OF OLIGOSACCHARIDES [J].
BLATTER, G ;
BEAU, JM ;
JACQUINET, JC .
CARBOHYDRATE RESEARCH, 1994, 260 (02) :189-202
[6]
BUGG TDH, 1994, FEMS MICROBIOL LETT, V119, P255
[7]
THE PARA-METHOXYBENZYL GROUP AS PROTECTIVE GROUP OF THE ANOMERIC CENTER - SELECTIVE CONVERSIONS OF HYDROXY-GROUPS INTO BROMO GROUPS IN PARA-METHOXYBENZYL 2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDE [J].
CLASSON, B ;
GAREGG, PJ ;
SAMUELSSON, B .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (05) :419-422
[8]
PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[9]
2-DEOXY-2-TRICHLOROACETAMIDO-D-GLUCOPYRANOSE DERIVATIVES IN OLIGOSACCHARIDE SYNTHESIS - FROM HYALURONIC-ACID TO CHONDROITIN 4-SULFATE TRISACCHARIDES [J].
COUTANT, C ;
JACQUINET, JC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (12) :1573-1581
[10]
1,3,4,6-TETRA-O-ACETYL-2-CHLOROACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE AS A GLYCOSYL DONOR IN SYNTHESES OF OLIGOSACCHARIDES [J].
DASGUPTA, F ;
ANDERSON, L .
CARBOHYDRATE RESEARCH, 1990, 202 :239-255