Synthesis and evaluation of new 4-phospho-D-erythronic acid derivatives as competitive inhibitors of spinach ribose-5-phosphate isomerase

被引：13

作者：

Burgos, E ^{[1
]}

Salmon, L ^{[1
]}

机构：

[1] Univ Paris 11, CNRS, Inst Chim Mol & Mat, Lab Chim Bioorgan & Bioinorgan,UMR 8124, F-91405 Orsay, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 04期

关键词：

phosphate sugars; enzyme inhibitors; hydroxamic acids; hydroxamates;

D O I：

10.1016/j.tetlet.2003.11.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper reports the synthesis of new 4-phospho-D-erythronic acid derivatives, namely 4-phospho-D-erythronohydroxamic acid (1). 4-phospho-D-erythronohydrazide (2), and 4-phospho-D-erythronamide (3), and their kinetic evaluation as new competitive inhibitors of the isomerization reaction between D-ribose 5-phosphate and D-ribulose 5-phosphate catalyzed by spinach ribose-5-phosphate isomerase (RPI). By comparison to the only known RPI inhibitor, 4-phospho-D-erythronate (4, K-i = 28 muM, K-m/K-i = 270). the hydroxamic acid 1, obtained by an eight-step synthesis from D-arabinose, appears as a new potent high-energy intermediate analogue inhibitor of the isomerization reaction (K-i = 29 muM, K-m/K-i = 260). (C) 2003 Elsevier Ltd. All rights reserved.

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页码：753 / 756

页数：4

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