Anomer-selective inhibition of glycosidases using aminocyclopentanols

被引：33

作者：

Leroy, E ^{[1
]}

Raymond, JL ^{[1
]}

机构：

[1] Univ Bern, Dept Biochem & Chem, CH-3012 Bern, Switzerland

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 05期

关键词：

D O I：

10.1021/ol990754m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] (1S,2S,3S,4R,5R)-4-Amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol 1 is prepared stereoselectively from D-lyxose and displays anomer selective inhibition for beta galactosidase (K-i = 3.0 x 10(-6) M) and beta-glucosidase (K-i = 1.5 x 10(-7) M), over alpha-galactosidase (K-i = 2.3 x 10(-5) M) and a glucosidase (IC50 = 1.0 x 10(-4) M), There is no observable cross-reactivity with alpha-mannosidase, beta-mannosidase, or alpha-L-fucosidase.

引用

页码：775 / 777

页数：3

共 19 条

[1]

ALI SM, 1990, TETRAHEDRON LETT, V31, P1509

[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] Comparison of a beta-glucosidase and a beta-mannosidase from the hyperthermophilic archaeon Pyrococcus furiosus - Purification, characterization, gene cloning, and sequence analysis [J].

Bauer, MW ;

Bylina, EJ ;

Swanson, RV ;

Kelly, RM .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (39) :23749-23755

[4]

Blaser A, 1999, HELV CHIM ACTA, V82, P760

[5]

Blattner R, 1996, CARBOHYD RES, V294, P29

[6] SYNTHESES OF THE FUNGICIDE/INSECTICIDE ALLOSAMIDIN AND A STRUCTURAL ISOMER [J].

BLATTNER, R ;

FURNEAUX, RH ;

KEMMITT, T ;

TYLER, PC ;

FERRIER, RJ ;

TIDEN, AK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23) :3411-3421

[7] Synthesis of trehazolin from D-glucose [J].

Boiron, A ;

Zillig, P ;

Faber, D ;

Giese, B .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :5877-5882

[8] 1-aza sugars, apparent transition state analogues of equatorial glycoside formation/cleavage [J].

Bols, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (01) :1-8

[9]

DAVIES G, 1987, COMPREHENSIVE BIOL C, P119

[10]

de Gracia IS, 1998, J ORG CHEM, V63, P5883

← 1 2 →