Triazole carboxylic acids as anionic sugar mimics? Inhibition of glycogen phosphorylase by a D-glucotriazole carboxylate

被引：57

作者：

Krulle, T

delaFuente, C

Pickering, L

Aplin, RT

Tsitsanou, KE

Zographos, SE

Oikonomakos, NG

Nash, RJ

Griffiths, RC

Fleet, GWJ

机构：

[1] UNIV OXFORD,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND

[2] NATL HELLEN RES FDN,INST BIOL RES & BIOTECHNOL,ATHENS 11635,GREECE

[3] INST GRASSLAND & ENVIRONM RES,ABERYSTWYTH SY23 3EB,CARDIGAN,WALES

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 22期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0957-4166(97)00561-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Triazole-carboxylic acids related to D-glucose and D-galactose may be prepared by intramolecular [1,3]-dipolar cycloadditions of azides to unsaturated esters, followed by bromine oxidation of the resulting triazoline. Such materials may provide a series of anionic mimics of carbohydrates. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：3807 / 3820

页数：14

相关论文

共 32 条

[1] NAGSTATIN, A NEW INHIBITOR OF N-ACETYL-BETA-D-GLUCOSAMINIDASE, PRODUCED BY STREPTOMYCES-AMAKUSAENSIS MG846-FF3 - TAXONOMY, PRODUCTION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITIES [J].

AOYAGI, T ;

SUDA, H ;

UOTANI, K ;

KOJIMA, F ;

AOYAMA, T ;

HORIGUCHI, K ;

HAMADA, M ;

TAKEUCHI, T .

JOURNAL OF ANTIBIOTICS, 1992, 45 (09) :1404-1408

[2] THE STRUCTURE OF NAGSTATIN, A NEW INHIBITOR OF N-ACETYL-BETA-D-GLUCOSAMINIDASE [J].

AOYAMA, T ;

NAGANAWA, H ;

SUDA, H ;

UOTANI, K ;

AOYAGI, T ;

TAKEUCHI, T .

JOURNAL OF ANTIBIOTICS, 1992, 45 (09) :1557-1558

[3]

Bell AA, 1997, SYNLETT, P1077

[4] ANALOGS OF SIALIC ACIDS AS POTENTIAL SIALIDASE INHIBITORS - SYNTHESIS OF 2-C-HYDROXYMETHYL DERIVATIVES OF N-ACETYL-6-AMINO-2,6-DIDEOXY-NEURAMINIC ACID [J].

BERNET, B ;

MURTY, ARCB ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1990, 73 (04) :940-958

[5] 7-carbon mimics of D-glucose and L-fucose: Activation by 6R-, and inactivation by 6S, -6C-methylglucose of glycogen synthase: Inhibition of glucokinase and/or glucose-6-phosphatase [J].

Bleriot, Y ;

Smelt, KH ;

Cadefau, J ;

Bollen, M ;

Stalmans, W ;

Biggadike, K ;

Johnson, LN ;

Oikonomakos, NG ;

Lane, AL ;

Crook, S ;

Watkin, DJ ;

Fleet, GWJ .

TETRAHEDRON LETTERS, 1996, 37 (39) :7155-7158

[6] TETRAZOLES OF MANNO-PYRANOSES AND RHAMNO-PYRANOSES - INHIBITION OF GLYCOSIDASES BY TETRAZOLES AND OTHER MANNOSE MIMICS [J].

BRANDSTETTER, TW ;

DAVIS, B ;

HYETT, D ;

SMITH, C ;

HACKETT, L ;

WINCHESTER, BG ;

FLEET, GWJ .

TETRAHEDRON LETTERS, 1995, 36 (41) :7511-7514

[7] A NEW ROUTE TO CHIRAL HYDROXYPYRROLIDINES FROM D-ERYTHROSE VIA INTRAMOLECULAR 1,3-CYCLOADDITION [J].

BUCHANAN, JG ;

EDGAR, AR ;

HEWITT, BD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (11) :2371-2376

[8] TETRAZOLES OF MANNO-FURANOSES AND RHAMNO-FURANOSES [J].

DAVIS, B ;

BRANDSTETTER, TW ;

SMITH, C ;

HACKETT, L ;

WINCHESTER, BG ;

FLEET, GWJ .

TETRAHEDRON LETTERS, 1995, 36 (41) :7507-7510

[9]

delaFuente C, 1997, SYNLETT, P485

[10] CONFIGURATIONALLY SELECTIVE TRANSITION-STATE ANALOG INHIBITORS OF GLYCOSIDASES - A STUDY WITH NOJIRITETRAZOLES, A NEW CLASS OF GLYCOSIDASE INHIBITORS [J].

ERMERT, P ;

VASELLA, A ;

WEBER, M ;

RUPITZ, K ;

WITHERS, SG .

CARBOHYDRATE RESEARCH, 1993, 250 (01) :113-128

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