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).
Original language | English (US) |
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Pages (from-to) | 753-756 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 45 |
Issue number | 4 |
DOIs | |
State | Published - Jan 19 2004 |
Externally published | Yes |
Keywords
- Enzyme inhibitors
- Hydroxamates
- Hydroxamic acids
- Phosphate sugars
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry