Tags

Type your tag names separated by a space and hit enter

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.
Org Biomol Chem. 2003 Dec 21; 1(24):4367-72.OB

Abstract

(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.

Authors+Show Affiliations

Meyer O
Université Louis Pasteur, CNRS UMR 7123, Institut Le Bel, 4 rue Blaise Pascal, 67070 Strasbourg Cedex, France.
Grosdemange-Billiard C
No affiliation info available
Tritsch D
No affiliation info available
Rohmer M
No affiliation info available

MeSH

Aldose-Ketose IsomerasesErythritolEscherichia coliKineticsMagnetic Resonance SpectroscopyMultienzyme ComplexesOrganophosphorus CompoundsOxidoreductasesPentosephosphatesPolyisoprenyl PhosphatesSugar Phosphates

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

14685307

Citation

Meyer, Odile, et al. "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, vol. 1, no. 24, 2003, pp. 4367-72.
Meyer O, Grosdemange-Billiard C, Tritsch D, et al. 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. Org Biomol Chem. 2003;1(24):4367-72.
Meyer, O., Grosdemange-Billiard, C., Tritsch, D., & Rohmer, M. (2003). 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, 1(24), 4367-72.
Meyer O, et al. 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. Org Biomol Chem. 2003 Dec 21;1(24):4367-72. PubMed PMID: 14685307.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 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. AU - Meyer,Odile, AU - Grosdemange-Billiard,Catherine, AU - Tritsch,Denis, AU - Rohmer,Michel, Y1 - 2003/11/06/ PY - 2003/12/20/pubmed PY - 2004/3/9/medline PY - 2003/12/20/entrez SP - 4367 EP - 72 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 1 IS - 24 N2 - (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. SN - 1477-0520 UR - https://www.unboundmedicine.com/medline/citation/14685307/Isoprenoid_biosynthesis_via_the_MEP_pathway__Synthesis_of__34__34_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_ DB - PRIME DP - Unbound Medicine ER -