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) |
|---|---|
| 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
Fingerprint Dive into the research topics of 'Synthesis and evaluation of new 4-phospho-D-erythronic acid derivatives as competitive inhibitors of spinach ribose-5-phosphate isomerase'. Together they form a unique fingerprint.
Cite this
Burgos, E., & Salmon, L. (2004). Synthesis and evaluation of new 4-phospho-D-erythronic acid derivatives as competitive inhibitors of spinach ribose-5-phosphate isomerase. Tetrahedron Letters, 45(4), 753-756. https://doi.org/10.1016/j.tetlet.2003.11.038