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
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.
引用
收藏
页码:407 / 409
页数:3
相关论文
共 13 条
[11]   Synthesis of (2R)-2-bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid [J].
Manthey, MK ;
GonzalezBello, C ;
Abell, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (05) :625-628
[12]   OBSERVATION OF AN IMINE INTERMEDIATE ON DEHYDROQUINASE BY ELECTROSPRAY MASS-SPECTROMETRY [J].
SHNEIER, A ;
KLEANTHOUS, C ;
DEKA, R ;
COGGINS, JR ;
ABELL, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9416-9418
[13]   SHIKIMATE PATHWAY .4. STEREOCHEMISTRY OF 3-DEHYDROQUINATE DEHYDRATASE REACTION AND OBSERVATIONS ON 3-DEHYDROQUINATE SYNTHETASE [J].
TURNER, MJ ;
SMITH, BW ;
HASLAM, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (01) :52-55