Isoprenoid biosynthesis via the MEP pathway. Synthesis of (3R,4S)-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,10.1039/B312193C

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Isoprenoid biosynthesis via the MEP pathway. Synthesis of (3R,4S)-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

Odile Meyer,Catherine Grosdemange-Billiard,Denis Tritsch,Michel Rohmer

Organic & Biomolecular Chemistry Pub Date : 11/06/2003 00:00:00 , DOI:10.1039/B312193C

Abstract

(3R,4S)-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-O-benzylidene-D-threitol by a seven-step sequence. This phosphonate did not affect the growth of Escherichiacoli. It did not inhibit the 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), but was converted by this enzyme into (3R,4R)-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.