N-linked carba-disaccharides as potential inhibitors of glucosidases I and II

被引：10

作者：

Carvalho, I ^{[1
]}

Haines, AH ^{[1
]}

机构：

[1] Univ E Anglia, Sch Chem Sci, Norwich NR4 7TJ, Norfolk, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 13期

关键词：

D O I：

10.1039/a902826i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An N-linked pseudodisaccharide 2 containing an inositol moiety in place of a glycopyranosyl residue has been synthesised to mimic the disaccharide unit, 3-O-(alpha-D-glucopyranosyl)-D-glucopyranose cleaved by glucosidase II during glycoprotein processing. Its inhibitory action towards yeast alpha-glucosidase was inferior to that of 1-deoxynojirmycin, a known inhibitor of glucosidase II. An attempt to prepare the analogous 2-N-linked compound 1 as an inhibitor of glucosidase I led to the novel N-phenyl derivative 11 of 2-amino-2-deoxy-D-glucopyranose.

引用

页码：1795 / 1800

页数：6

共 25 条

[1]

Albein A. D., 1987, ANNU REV BIOCHEM, V56, P497

[2] TRANSFER HYDROGENATION - CONVENIENT METHOD FOR REMOVAL OF SOME COMMONLY USED PROTECTING GROUPS IN PEPTIDE-SYNTHESIS [J].

ANANTHARAMAIAH, GM ;

SIVANANDAIAH, KM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (05) :490-491

[3] THE ABSOLUTE-CONFIGURATION OF (+)-1,2,4,5,6-PENTA-O-BENZYL-MYO-INOSITOL [J].

ANEJA, R ;

ANEJA, S ;

PATHAK, VP ;

IVANOVA, PT .

TETRAHEDRON LETTERS, 1994, 35 (33) :6061-6062

[4] SYNTHESIS OF D-MYO-INOSITOL AND L-MYO-INOSITOL 1-PHOSPHOROTHIOATE, SUBSTRATES FOR INOSITOL MONOPHOSPHATASE [J].

BAKER, GR ;

BILLINGTON, DC ;

GANI, D .

TETRAHEDRON, 1991, 47 (23) :3895-3908

[5] 1-aza sugars, apparent transition state analogues of equatorial glycoside formation/cleavage [J].

Bols, M .

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

[6]

CARSON JF, 1981, SYNTHESIS-STUTTGART, P269

[7] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ACYCLIC ANALOGS OF NOJIRIMYCIN [J].

FOWLER, PA ;

HAINES, AH ;

TAYLOR, RJK ;

CHRYSTAL, EJT ;

GRAVESTOCK, MB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (16) :2229-2235

[8] Synthesis and evaluation of a 5-membered isoiminosugar as glycosidase inhibitor [J].

Godskesen, M ;

Lundt, I .

TETRAHEDRON LETTERS, 1998, 39 (32) :5841-5844

[9] INTERFERENCE WITH HIV-INDUCED SYNCYTIUM FORMATION AND VIRAL INFECTIVITY BY INHIBITORS OF TRIMMING GLUCOSIDASE [J].

GRUTERS, RA ;

NEEFJES, JJ ;

TERSMETTE, M ;

DEGOEDE, REY ;

TULP, A ;

HUISMAN, HG ;

MIEDEMA, F ;

PLOEGH, HL .

NATURE, 1987, 330 (6143) :74-77

[10] NITROGEN-CONTAINING CARBOHYDRATE DERIVATIVES .4. SOME AZIDO- AND EPIMENO-SUGARS [J].

GUTHRIE, RD ;

MURPHY, D .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (NOV) :5288-&

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