Flexible enantiodivergent synthesis and biological activity of mannostatin analogues, new cyclitol glycosidase inhibitors

被引：23
作者：
Nishimura, Y
Umezawa, Y
Adachi, H
Kondo, S
Takeuchi, T
机构：
[1] Institute of Microbial Chemistry, Shinagawa-ku, Tokyo 141
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 02期
关键词：
D O I：
10.1021/jo951126v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Mannostatin A (1) is a new cyclitol inhibitor of glycoprotein processing. 2-Epimannostatin A (12) and its enantiomer (13) as well as their positional isomers (14, 15) were designed for probing structure-activity relationships in this class of glycosidase inhibitors. The analogues have been synthesized from (S)-4-((tert-butyldimethylsilyl)oxy)-2-cyclopentenone by an enantiodivergent strategy in a totally stereospecific fashion. Compound 13 showed inhibition against almond P-glucosidase and is shown to be a topographical analogue of beta-D-glucopyranoside.
引用
收藏
页码：480 / 488
页数：9
相关论文
共 44 条
[1]   CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].
ALLINGER, NL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134
[2]   MANNOSTATIN-A AND MANNOSTATIN-B - NEW INHIBITORS OF ALPHA-D-MANNOSIDASE, PRODUCED BY STREPTOVERTICILLIUM-VERTICILLUS VAR QUINTUM ME3-AG3 - TAXONOMY, PRODUCTION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITIES [J].
AOYAGI, T ;
YAMAMOTO, T ;
KOJIRI, K ;
MORISHIMA, H ;
NAGAI, M ;
HAMADA, M ;
TAKEUCHI, T ;
UMEZAWA, H .
JOURNAL OF ANTIBIOTICS, 1989, 42 (06) :883-889
[3]  
ATSUMI S, 1993, CANCER RES, V53, P4896
[4]   SPECTROSCOPIC INVESTIGATION OF SWAINSONINE - ALPHA-MANNOSIDASE INHIBITOR ISOLATED FROM SWAINSONA-CANESCENS [J].
COLEGATE, SM ;
DORLING, PR ;
HUXTABLE, CR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (10) :2257-2264
[5]  
DENIS JW, 1986, CANCER RES, V46, P5131
[6]   INHIBITORS OF THE BIOSYNTHESIS AND PROCESSING OF N-LINKED OLIGOSACCHARIDE CHAINS [J].
ELBEIN, AD .
ANNUAL REVIEW OF BIOCHEMISTRY, 1987, 56 :497-534
[7]  
ELBEIN AD, 1985, BIOCHEM J, V232, P759
[8]   HYDROXY-STEROIDS .6. REACTIONS OF OLEFINS WITH SILVER SALTS AND IODINE [J].
ELLINGTON, PS ;
HEY, DG ;
MEAKINS, GD .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (15) :1327-+
[9]   ISOLATION OF 1,5-DIDEOXY-1,5-IMINO-DEUTERIUM-MANNITOL FROM CULTURE BROTH OF STREPTOMYCES SPECIES [J].
EZURE, Y ;
OJIMA, N ;
KONNO, K ;
MIYAZAKI, K ;
YAMADA, N ;
SUGIYAMA, M ;
ITOH, M ;
NAKAMURA, T .
JOURNAL OF ANTIBIOTICS, 1988, 41 (08) :1142-1144
[10]   POTENT COMPETITIVE-INHIBITION OF ALPHA-GALACTOSIDASE AND ALPHA-GLUCOSIDASE ACTIVITY BY 1,4-DIDEOXY-1,4-IMINOPENTITOLS - SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL AND OF BOTH ENANTIOMERS OF 1,4-DIDEOXY-1,4-IMINOARABINITOL [J].
FLEET, GWJ ;
NICHOLAS, SJ ;
SMITH, PW ;
EVANS, SV ;
FELLOWS, LE ;
NASH, RJ .
TETRAHEDRON LETTERS, 1985, 26 (26) :3127-3130
12345