SYNTHESIS OF PSEUDO-OLIGOSACCHARIDE GLYCOSIDASE INHIBITORS .7. SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF METHYL OLIGOBIOSAMINIDE AND SOME DEOXY ISOMERS THEREOF

被引：16

作者：

SHIBATA, Y ^{[1
]}

KOSUGE, Y ^{[1
]}

OGAWA, S ^{[1
]}

机构：

[1] KEIO UNIV,FAC SCI & TECHNOL,DEPT APPL CHEM,KOHOKU KU,YOKOHAMA,KANAGAWA 223,JAPAN

来源：

CARBOHYDRATE RESEARCH | 1990年 / 199卷 / 01期

关键词：

D O I：

10.1016/0008-6215(90)84091-8

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：

Methyl oligobiosaminide (1) the core structure of oligostatin C, and five analogues, the 6-hydroxy-(2), 2-deoxy- (3), 2-deoxy-6-hydroxy- (4), 3-deoxy- (5), and 3-deoxy-6-hydroxy derivatives (6), were synthesized by coupling the protected pseudo-sugar epoxide 46 with suitable methyl 4-amino-4-deoxy-a-d-hexopyranoside derivatives. Compounds 3 and 6 showed notable inhibitory activity against a-d-glucosidase and a-d-mannosidase, respectively, whereas compound 1 had almost no activity. © 1990.

引用

页码：37 / 54

页数：18

共 15 条

[1] THE FORMATION OF BRANCHED-CHAIN DEOXYPENTOFURANOSIDES BY RING CONTRACTION IN THE REDUCTIVE DESULFONYLOXYLATION OF HEXOPYRANOSIDE P-TOLUENESULFONATES [J].

BAER, HH ;

ASTLES, DJ ;

CHIN, HC ;

SIEMSEN, L .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (02) :432-439

[2] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

MCCOMBIE, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585

[3] REACTIONS OF PARA-TOLUENESULFONATES WITH LITHIUM TRIETHYLBOROHYDRIDE - VISIBLE AND HIDDEN REARRANGEMENTS [J].

BINKLEY, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5646-5649

[4] OLIGOSTATINS, NEW ANTIBIOTICS WITH AMYLASE INHIBITORY ACTIVITY .1. PRODUCTION, ISOLATION AND CHARACTERIZATION [J].

ITOH, J ;

OMOTO, S ;

SHOMURA, T ;

OGINO, H ;

IWAMATSU, K ;

INOUYE, S ;

HIDAKA, H .

JOURNAL OF ANTIBIOTICS, 1981, 34 (11) :1424-1428

[5] 2-SUBSTITUTED METHYL ALPHA-D-GALACTOPYRANOSIDES - SYNTHESIS AND BINDING-AFFINITY FOR THE A AND B SUBUNITS OF THE GRIFFONIA-SIMPLICIFOLIA-I ISOLECTINS [J].

KAIFU, R ;

PLANTEFABER, LC ;

GOLDSTEIN, IJ .

CARBOHYDRATE RESEARCH, 1985, 140 (01) :37-49

[6]

MIYAMOTO Y, 1988, J CHEM SOC P1, P2675

[7] NOVEL GLYCOSIDASE INHIBITORS, NOJIRIMYCIN-B AND D-MANNONIC-DELTA-LACTAM - ISOLATION, STRUCTURE DETERMINATION AND BIOLOGICAL PROPERTY [J].

NIWA, T ;

TSURUOKA, T ;

GOI, H ;

KODAMA, Y ;

ITOH, J ;

INOUYE, S ;

YAMADA, Y ;

NIIDA, T ;

NOBE, M ;

OGAWA, Y .

JOURNAL OF ANTIBIOTICS, 1984, 37 (12) :1579-1586

[8] SYNTHESIS OF PSEUDO-OLIGOSACCHARIDIC GLYCOSIDASE INHIBITORS .3. SYNTHESIS OF SOME ANALOGS OF METHYL DEHYDRO-OLIGOBIOSAMINIDE (ACARVIOSIN) [J].

OGAWA, S ;

YASUDA, K ;

TAKAGAKI, T ;

IWASAWA, Y ;

SUAMI, T .

CARBOHYDRATE RESEARCH, 1985, 141 (02) :329-334

[9] SYNTHESIS OF PSEUDO-OLIGOSACCHARIDE GLYCOSIDASE INHIBITORS .4. SYNTHESIS OF A CORE STRUCTURE OF THE ANTIBIOTIC OLIGOSTATIN [J].

OGAWA, S ;

IWASAWA, Y ;

TOYOKUNI, T ;

SUAMI, T .

CARBOHYDRATE RESEARCH, 1985, 144 (01) :155-162

[10] TOTAL SYNTHESIS OF (+)-VALIDAMYCIN-B [J].

OGAWA, S ;

MIYAMOTO, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (24) :1843-1844

← 1 2 →