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

Emmanuel S. Burgos, Laurent Salmon

Research output: Contribution to journal › Article

10 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)753-756
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number4
DOIs
StatePublished - Jan 19 2004
Externally publishedYes

Fingerprint

Spinacia oleracea
Isomerization
Hydroxamic Acids
Derivatives
Arabinose
Kinetics
erythronic acid
ribosephosphate isomerase
4-phosphoerythronamide
4-phosphoerythronohydroxamic acid
ribose-5-phosphate
ribulose 5-phosphate

Keywords

  • Enzyme inhibitors
  • Hydroxamates
  • Hydroxamic acids
  • Phosphate sugars

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and evaluation of new 4-phospho-D-erythronic acid derivatives as competitive inhibitors of spinach ribose-5-phosphate isomerase. / Burgos, Emmanuel S.; Salmon, Laurent.

In: Tetrahedron Letters, Vol. 45, No. 4, 19.01.2004, p. 753-756.

Research output: Contribution to journal › Article

Burgos, ES & 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, vol. 45, no. 4, pp. 753-756. https://doi.org/10.1016/j.tetlet.2003.11.038
Burgos ES, Salmon L. Synthesis and evaluation of new 4-phospho-D-erythronic acid derivatives as competitive inhibitors of spinach ribose-5-phosphate isomerase. Tetrahedron Letters. 2004 Jan 19;45(4):753-756. https://doi.org/10.1016/j.tetlet.2003.11.038
Burgos, Emmanuel S. ; Salmon, Laurent. / Synthesis and evaluation of new 4-phospho-D-erythronic acid derivatives as competitive inhibitors of spinach ribose-5-phosphate isomerase. In: Tetrahedron Letters. 2004 ; Vol. 45, No. 4. pp. 753-756.
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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).

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