Emmanuel S. Burgos, L. Salmon
Jan 19, 2004
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0
Influential Citations
13
Citations
Journal
Tetrahedron Letters
Abstract
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 =28 μM, 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 μM, K m / K i =260).