SYNTHESIS OF, AND LACK OF INHIBITION OF A RHAMNOSIDASE BY, BOTH ENANTIOMERS OF DEOXYRHAMNOJIRIMYCIN AND RHAMNONOLACTAM - BETA-MANNOSIDASE INHIBITION BY DELTA-LACTAMS

被引:56
作者
FAIRBANKS, AJ
CARPENTER, NC
FLEET, GWJ
RAMSDEN, NG
DEBELLO, IC
WINCHESTER, BG
ALDAHER, SS
NAGAHASHI, G
机构
[1] UNIV LONDON,INST CHILD HLTH,DIV BIOCHEM S METAB,LONDON WC1N 1EH,ENGLAND
[2] USDA ARS,EASTERN REG RES CTR,PHILADELPHIA,PA 19118
关键词
D O I
10.1016/0040-4020(92)85012-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of both enantiomers of deoxyrhamnojirimycin and rhamnonolactam from D- and L-gulonolactones are described. The effects as inhibitors of the enantiomeric deoxyrhamnojirimycins and rhamnonolactams on human liver glycosidases are compared with deoxymannojirimycin and mannonolactam. No significant inhibition of the activity of naringinase (an alpha-L-rhamnosidase) was caused by any of these compounds.
引用
收藏
页码:3365 / 3376
页数:12
相关论文
共 38 条
[11]   ISOLATION AND STRUCTURE OF AN UNUSUAL CYCLIC AMINO ALDITOL FROM A LEGUME [J].
FELLOWS, LE ;
BELL, EA ;
LYNN, DG ;
PILKIEWICZ, F ;
MIURA, I ;
NAKANISHI, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (22) :977-978
[12]  
FLEET GWJ, 1990, CIBA F SYMP, V154, P112
[13]   DELTA-LACTAMS - SYNTHESIS FROM D-GLUCOSE, AND PRELIMINARY EVALUATION AS A FUCOSIDASE INHIBITOR, OF L-FUCONIC-DELTA-LACTAM [J].
FLEET, GWJ ;
RAMSDEN, NG ;
DWEK, RA ;
RADEMACHER, TW ;
FELLOWS, LE ;
NASH, RJ ;
GREEN, DS ;
WINCHESTER, B .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (07) :483-485
[14]   DESIGN SYNTHESIS AND PRELIMINARY EVALUATION OF A POTENT ALPHA-MANNOSIDASE INHIBITOR - 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL [J].
FLEET, GWJ ;
SMITH, PW ;
EVANS, SV ;
FELLOWS, LE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (18) :1240-1241
[15]   SHORT SYNTHESES OF D-DEOXYMANNOJIRIMYCIN AND D-MANNONOLACTAM FROM L-GULONOLACTONE AND OF L-DEOXYMANNOJIRIMYCIN AND L-MANNONOLACTAM FROM D-GULONOLACTONE [J].
FLEET, GWJ ;
RAMSDEN, NG ;
WITTY, DR .
TETRAHEDRON LETTERS, 1988, 29 (23) :2871-2874
[16]   PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND MANNONOLACTAM FROM L-GULONOLACTONE - SYNTHESIS OF L-DEOXYMANNOJIRIMYCIN AND L-MANNONOLACTAM FROM D-GULONOLACTONE [J].
FLEET, GWJ ;
RAMSDEN, NG ;
WITTY, DR .
TETRAHEDRON, 1989, 45 (01) :319-326
[18]   NOVEL MANNOSIDASE INHIBITOR BLOCKING CONVERSION OF HIGH MANNOSE TO COMPLEX OLIGOSACCHARIDES [J].
FUHRMANN, U ;
BAUSE, E ;
LEGLER, G ;
PLOEGH, H .
NATURE, 1984, 307 (5953) :755-758
[19]  
GALLONMO RA, 1983, CARBOHYD RES, V119, P231
[20]   1ST SYNTHESIS OF (1R,2R,3S,9S,9AR)-1,2,3,9-TETRAHYDROXY-QUINOLIZIDINE, A NOVEL ISOSTERIC HOMOLOG OF THE GLUCOSIDASE INHIBITOR CASTANOSPERMINE [J].
GRADNIG, G ;
BERGER, A ;
GRASSBERGER, V ;
STUTZ, AE ;
LEGLER, G .
TETRAHEDRON LETTERS, 1991, 32 (37) :4889-4892