SYNTHESIS OF MUROPEPTIDE CONJUGATES OF 2,3-DIDEOXY-BETA-D-MANNO-2-OCTULOSONIC ACID

被引:2
作者
LERCHEN, HG [1 ]
KROLL, HP [1 ]
机构
[1] BAYER AG,INST CHEMOTHERAPIE,W-5600 WUPPERTAL,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 12期
关键词
D O I
10.1002/anie.199116821
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Although an inhibitor of the bacterial lipopolysaccharide biosynthesis, the title compound 2-deoxy-beta-KDO (1) cannot pass through the bacterial membrane. The coupling of the carboxy function with peptidic carriers creates conjugates (prodrugs) like 2, which can be actively transported into the cell. Their stability in vivo can be modulated by modifying the potential cleavage sites.
引用
收藏
页码:1682 / 1684
页数:3
相关论文
共 18 条
[1]   MUTUAL PRO-DRUGS OF BETA-LACTAM ANTIBIOTICS AND BETA-LACTAMASE INHIBITORS [J].
BALTZER, B ;
BINDERUP, E ;
VONDAEHNE, W ;
GODTFREDSEN, WO ;
HANSEN, K ;
NIELSEN, B ;
SORENSEN, H ;
VANGEDAL, S .
JOURNAL OF ANTIBIOTICS, 1980, 33 (10) :1183-1192
[2]  
BUNDGAARD H, 1987, BIOREVERSIBLE CARRIE, P13
[3]   DESIGN AND SYNTHESIS OF PEPTIDE DERIVATIVES OF A 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) ANALOG AS NOVEL ANTIBACTERIAL AGENTS ACTING UPON LIPOPOLYSACCHARIDE BIOSYNTHESIS [J].
CLAESSON, A ;
JANSSON, AM ;
PRING, BG ;
HAMMOND, SM ;
EKSTROM, B .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (12) :2309-2313
[4]   A 2-DEOXY ANALOG OF KDO AS THE 1ST INHIBITOR OF THE ENZYME CMP-KDO SYNTHETASE [J].
CLAESSON, A ;
LUTHMAN, K ;
GUSTAFSSON, K ;
BONDESSON, G .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1987, 143 (03) :1063-1068
[5]  
GHALAMBOR MA, 1966, J BIOL CHEM, V241, P3216
[6]   PREPARATION OF MERRIFIELD-RESINS THROUGH TOTAL ESTERIFICATION WITH CESIUM SALTS [J].
GISIN, BF .
HELVETICA CHIMICA ACTA, 1973, 56 (05) :1476-1482
[7]  
GOLDMAN R, 1987, NATURE, V329, P730
[8]   UPTAKE OF CELL-WALL PEPTIDES BY SALMONELLA-TYPHIMURIUM AND ESCHERICHIA-COLI [J].
GOODELL, EW ;
HIGGINS, CF .
JOURNAL OF BACTERIOLOGY, 1987, 169 (08) :3861-3865
[9]   RECYCLING OF MUREIN BY ESCHERICHIA-COLI [J].
GOODELL, EW .
JOURNAL OF BACTERIOLOGY, 1985, 163 (01) :305-310
[10]  
KOHLBRENNER WE, 1985, J BIOL CHEM, V260, P4695