Home
Resources
Publications
Synthesis and Biological Evaluation With Plant Cells of New Fosmidomycin Analogues Containing a Benzoxazolone or Oxazolopyridinone Ring

Synthesis and Biological Evaluation With Plant Cells of New Fosmidomycin Analogues Containing a Benzoxazolone or Oxazolopyridinone Ring

Martine Courtois, Zoia Mincheva, Françoise Andreu, Marc Rideau, Marie-Claude Viaud-Massuard

J Enzyme Inhib Med Chem. 2004 Dec;19(6):559-65.

PMID: 15662959

Abstract:

Fosmidomycin, 3-(N-formyl-N-hydroxyamido) propylphosphonic acid sodium salt, is an efficient inhibitor of 1-deoxy-D-xylulose-5-phosphate (DOXP) reductoisomerase, the second enzyme of the 2C-methyl-D-erythritol-4-phosphate (MEP) pathway notably present in Plasmodium species. We have synthesized a new series of analogues of fosmidomycin, containing a benzoxazolone, benzoxazolethione or oxazolopyridinone ring. As the MEP pathway is involved in the biosynthesis of all isoprenoids, accumulation of ajmalicine in Catharanthus roseus cells was chosen as a marker of monoterpenoid indole alkaloid (MIA) production. None of the twelve studied phosphonic esters 3 and phosphonic acids 4 affected periwinkle cell growth, but some of them (3c, 3e, 3g and 3h) showed a significant inhibition of ajmalicine accumulation: 45-85% at 125 microM. Surprisingly, this effect disappeared by conversion of 3c and 3g into the corresponding acids 4c and 4g, respectively.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
ALP190079186	1-Deoxy-D-xylulose-5-phosphate sodium salt		190079-18-6 (free acid)	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: