Irreversible inhibition of type I dehydroquinase by substrates for type II dehydroquinase

被引：9

作者：

Bello, CG

Harris, JM

Manthey, MK

Coggins, JR

Abell, C

机构：

[1] Univ Cambridge, Cambridge Ctr Mol Recognit, Chem Lab, Cambridge CB2 1EW, England

[2] Univ Glasgow, Dept Biochem, Glasgow G12 8QQ, Lanark, Scotland

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2000年 / 10卷 / 05期

基金：

英国生物技术与生命科学研究理事会; 英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0960-894X(00)00057-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Mechanistic differences between type I and type II dehydroquinases have been exploited in the design of type specific inhibitors. (2R)-2-Bromo-3-dehydroquinic acid (3), (2R)-2-fluoro-3-dehydroquinic acid (5) and 2-bromo-3-dehydroshikimic acid (4), all excellent substrates for type II dehydroquinase, are shown to be irreversible inhibitors of type I dehydroquinase. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

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收藏

页码：407 / 409

页数：3

相关论文

共 13 条

[1]

[Anonymous], [No title captured]

[2] PURIFICATION AND CHARACTERIZATION OF 3-DEHYDROQUINASE FROM ESCHERICHIA-COLI [J].

CHAUDHURI, S ;

LAMBERT, JM ;

MCCOLL, LA ;

COGGINS, JR .

BIOCHEMICAL JOURNAL, 1986, 239 (03) :699-704

[3] THE OVEREXPRESSION AND COMPLETE AMINO-ACID-SEQUENCE OF ESCHERICHIA-COLI 3-DEHYDROQUINASE [J].

DUNCAN, K ;

CHAUDHURI, S ;

CAMPBELL, MS ;

COGGINS, JR .

BIOCHEMICAL JOURNAL, 1986, 238 (02) :475-483

[4] THE MYCOBACTERIUM-TUBERCULOSIS SHIKIMATE PATHWAY GENES - EVOLUTIONARY RELATIONSHIP BETWEEN BIOSYNTHETIC AND CATABOLIC 3-DEHYDROQUINASES [J].

GARBE, T ;

SERVOS, S ;

HAWKINS, A ;

DIMITRIADIS, G ;

YOUNG, D ;

DOUGAN, G ;

CHARLES, I .

MOLECULAR & GENERAL GENETICS, 1991, 228 (03) :385-392

[5] GENE ORGANIZATION AND REGULATION IN THE QA (QUINIC ACID) GENE-CLUSTER OF NEUROSPORA-CRASSA [J].

GILES, NH ;

CASE, ME ;

BAUM, J ;

GEEVER, R ;

HUIET, L ;

PATEL, V ;

TYLER, B .

MICROBIOLOGICAL REVIEWS, 1985, 49 (03) :338-358

[6] Synthesis of 2-bromo- and 2-fluoro-3-dehydroshikimic acids and 2-bromo- and 2-fluoroshikimic acids using synthetic and enzymatic approaches [J].

González-Bello, C ;

Manthey, MK ;

Harris, JH ;

Hawkins, AR ;

Coggins, JR ;

Abell, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (05) :1591-1597

[7] DIFFERENT MECHANISTIC AND STEREOCHEMICAL COURSES FOR THE REACTIONS CATALYZED BY TYPE-I AND TYPE-II DEHYDROQUINASES [J].

HARRIS, J ;

KLEANTHOUS, C ;

COGGINS, JR ;

HAWKINS, AR ;

ABELL, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (13) :1080-1081

[8] Evidence from kinetic isotope studies for an enolate intermediate in the mechanism of type II dehydroquinases [J].

Harris, JM ;

GonzalezBello, C ;

Kleanthous, C ;

Hawkins, AR ;

Coggins, JR ;

Abell, C .

BIOCHEMICAL JOURNAL, 1996, 319 :333-336

[9] SHIKIMATE PATHWAY .1. INTRODUCTION - PREPARATION OF STEREOSPECIFICALLY LABELLED 2-DEUTERIO-DERIVATIVES OF 3-DEHYDROQUINIC ACID [J].

HASLAM, E ;

TURNER, MJ ;

SARGENT, D ;

THOMPSON, RS .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (08) :1489-&

[10] A COMPARISON OF THE ENZYMOLOGICAL AND BIOPHYSICAL PROPERTIES OF 2 DISTINCT CLASSES OF DEHYDROQUINASE ENZYMES [J].

KLEANTHOUS, C ;

DEKA, R ;

DAVIS, K ;

KELLY, SM ;

COOPER, A ;

HARDING, SE ;

PRICE, NC ;

HAWKINS, AR ;

COGGINS, JR .

BIOCHEMICAL JOURNAL, 1992, 282 :687-695