Synthesis and evaluation of a new inhibitor of phosphoglucose isomerases:: the enediolate analogue 5-phospho-D-arabinohydroxamate

被引：34

作者：

Hardré, R ^{[1
]}

Bonnette, C ^{[1
]}

Salmon, L ^{[1
]}

Gaudemer, A ^{[1
]}

机构：

[1] Univ Paris 11, CNRS URA 1384, Lab Chim Bioorgan & Bioinorgan, ICMO, F-91405 Orsay, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1998年 / 8卷 / 23期

关键词：

carbohydrates; enzyme inhibitors; hydroxamic acids; phosphoric acid and derive;

D O I：

10.1016/S0960-894X(98)00621-0

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Designed as a high energy intermediate analogue inhibitor of the potent chemotherapeutic target phosphoglucose isomerases, 5-phospho-D-arabinohydroxamate was efficiently synthesized in a two steps procedure. To date, it proved to be the strongest competitive inhibitor with respect to substrate D-fructose-6-phosphate (K-1 down to 98 nM and K-m/K-i values up to 513). A comparative inhibition study of this compound and other known strong inhibitors on phosphoglucose isomerases from three different sources is also reported. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3435 / 3438

页数：4

共 33 条

[1] DESIGN, SYNTHESIS, AND CHARACTERIZATION OF A POTENT XYLOSE ISOMERASE INHIBITOR, D-THREONOHYDROXAMIC ACID, AND HIGH-RESOLUTION X-RAY CRYSTALLOGRAPHIC STRUCTURE OF THE ENZYME-INHIBITOR COMPLEX [J].

ALLEN, KN ;

LAVIE, A ;

PETSKO, GA ;

RINGE, D .

BIOCHEMISTRY, 1995, 34 (11) :3742-3749

[2] OXALYL HYDROXAMATES AS REACTION-INTERMEDIATE ANALOGS FOR KETOL-ACID REDUCTOISOMERASE [J].

AULABAUGH, A ;

SCHLOSS, JV .

BIOCHEMISTRY, 1990, 29 (11) :2824-2830

[3] Synthesis of 5-phosphate-D-arabinohydroxamic acid, a potent transition state analogue inhibitor of 6-phosphate-D-glucose isomerases [J].

Bonnette, C ;

Salmon, L ;

Gaudemer, A .

TETRAHEDRON LETTERS, 1996, 37 (08) :1221-1224

[4] THERMODYNAMIC ASPECTS OF THE ACTION OF PHOSPHOHEXOSEISOMERASE [J].

BRUNS, F ;

OKADA, S .

NATURE, 1956, 177 (4498) :87-88

[5]

CHIRGWIN JM, 1975, J BIOL CHEM, V250, P7272

[6]

COLLINS KD, 1974, J BIOL CHEM, V249, P136

[7] STRUCTURE OF THE TRIOSEPHOSPHATE ISOMERASE PHOSPHOGLYCOLOHYDROXAMATE COMPLEX - AN ANALOG OF THE INTERMEDIATE ON THE REACTION PATHWAY [J].

DAVENPORT, RC ;

BASH, PA ;

SEATON, BA ;

KARPLUS, M ;

PETSKO, GA ;

RINGE, D .

BIOCHEMISTRY, 1991, 30 (24) :5821-5826

[8]

DYSON JED, 1968, J BIOL CHEM, V243, P1401

[9]

FILLELA X, 1991, TUMOR BIOL, V12, P360

[10] EVOLUTION OF GLYCOLYSIS [J].

FOTHERGILLGILMORE, LA ;

MICHELS, PAM .

PROGRESS IN BIOPHYSICS & MOLECULAR BIOLOGY, 1993, 59 (02) :105-235

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