Isoprenoid biosynthesis via the MEP pathway. Synthesis of (3,4)-3,4-dihydroxy-5-oxohexylphosphonic acid, an isosteric analogue of 1-deoxy-D-xylulose 5-phosphate, the substrate of the 1-deoxy-D-xylulose 5-phosphate reducto-isomerase

Organic & Biomolecular Chemistry
Odile MeyerMichel Rohmer


(3,4)-3,4-Dihydroxy-5-oxohexylphosphonic acid, an isosteric analogue of 1-deoxy-D-xylulose 5-phosphate (DXP), was obtained in enantiomerically pure form from (+)-2,3--benzylidene--threitol by a seven-step sequence. This phosphonate did not affect the growth of. It did not inhibit the 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), but was converted by this enzyme into (3,4)-3,4,5-trihydroxy-3-methylpentylphosphonic acid, an isosteric analogue of 2-C-methyl-D-erythritol 4-phosphate. The enzyme was, however, less efficient with the methylene phosphonate analogue than with the natural substrate.


Sep 30, 2004·Bioorganic & Medicinal Chemistry Letters·C Phaosiri, Philip J Proteau
Jun 20, 2008·Organic & Biomolecular Chemistry·Weidong Pan, Stéphane P Vincent
May 18, 2005·Biotechnology and Bioengineering·Min Jung KangSeon Won Kim
Nov 21, 2007·The Journal of Organic Chemistry·Chandraiah LagisettiRobert M Coates

Related Concepts

1-deoxy-D-xylulose 5-phosphate
YaeM protein, E coli
(3,4)-3,4-dihydroxy-5-oxohexylphosphonic acid
Alkalescens-Dispar Group
Multienzyme Complexes
In Vivo NMR Spectroscopy
Organopyrophosphorus Compounds

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