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

Emmanuel Burgos; Laurent Salmon

doi:10.1016/j.tetlet.2003.11.038

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

Emmanuel Burgos, Laurent Salmon

Biochemistry

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

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=28μM, 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=29μM, K_m/K_i=260).

Original language	English (US)
Pages (from-to)	753-756
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2003.11.038
State	Published - Jan 19 2004

Keywords

Enzyme inhibitors
Hydroxamates
Hydroxamic acids
Phosphate sugars

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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

abstract = "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, Ki=28μM, K m/Ki=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=29μM, Km/Ki=260).",

keywords = "Enzyme inhibitors, Hydroxamates, Hydroxamic acids, Phosphate sugars",

author = "Emmanuel Burgos and Laurent Salmon",

note = "Funding Information: E.B. is grateful to the Minist{\`e}re de l{\textquoteright}Education Nationale et de la Recherche for a grant (2001–2004).",

year = "2004",

month = jan,

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doi = "10.1016/j.tetlet.2003.11.038",

language = "English (US)",

volume = "45",

pages = "753--756",

journal = "Tetrahedron Letters",

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T1 - Synthesis and evaluation of new 4-phospho-D-erythronic acid derivatives as competitive inhibitors of spinach ribose-5-phosphate isomerase

AU - Burgos, Emmanuel

AU - Salmon, Laurent

N1 - Funding Information: E.B. is grateful to the Ministère de l’Education Nationale et de la Recherche for a grant (2001–2004).

PY - 2004/1/19

Y1 - 2004/1/19

N2 - 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, Ki=28μM, K m/Ki=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=29μM, Km/Ki=260).

AB - 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, Ki=28μM, K m/Ki=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=29μM, Km/Ki=260).

KW - Enzyme inhibitors

KW - Hydroxamates

KW - Hydroxamic acids

KW - Phosphate sugars

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