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Isoprenoid biosynthesis via the methylerythritol phosphate pathway: structural variations around phosphonate anchor and spacer of fosmidomycin, a potent inhibitor of deoxyxylulose phosphate reductoisomerase.
J Org Chem. 2010 May 21; 75(10):3203-7.JO

Abstract

Fosmidomycin and its analogue FR-900098 are potent inhibitors of 1-deoxy-d-xylulose 5-phosphate reducto-isomerase (DXR), the second enzyme of the MEP pathway for the biosynthesis of isoprenoids. This paper describes the synthesis of analogues of the two reverse phosphonohydroxamic acids 3 and 4, in which the length of the carbon spacer is modified, the N-methyl group of 3 is replaced by an ethyl group, and the phosphate group is replaced by potential isosteric moieties, i.e., sulfonate or carboxylate functionalities. The potential of the synthesized analogues to inhibit the E. coli DXR was evaluated.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zinglé C
Université de Strasbourg/CNRS, Strasbourg, UMR 7177, Institut Le Bel, 4 rue Blaise Pascal, 67070 Strasbourg, France.
Kuntz L
No affiliation info available
Tritsch D
No affiliation info available
Grosdemange-Billiard C
No affiliation info available
Rohmer M
No affiliation info available

MeSH

Aldose-Ketose IsomerasesEnzyme InhibitorsErythritolFosfomycinMolecular StructureMultienzyme ComplexesOrganophosphonatesOxidoreductasesStructure-Activity RelationshipSugar PhosphatesTerpenes

Pub Type(s)

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

Language

eng

PubMed ID

20429517

Citation

Zinglé, Catherine, et al. "Isoprenoid Biosynthesis Via the Methylerythritol Phosphate Pathway: Structural Variations Around Phosphonate Anchor and Spacer of Fosmidomycin, a Potent Inhibitor of Deoxyxylulose Phosphate Reductoisomerase." The Journal of Organic Chemistry, vol. 75, no. 10, 2010, pp. 3203-7.
Zinglé C, Kuntz L, Tritsch D, et al. Isoprenoid biosynthesis via the methylerythritol phosphate pathway: structural variations around phosphonate anchor and spacer of fosmidomycin, a potent inhibitor of deoxyxylulose phosphate reductoisomerase. J Org Chem. 2010;75(10):3203-7.
Zinglé, C., Kuntz, L., Tritsch, D., Grosdemange-Billiard, C., & Rohmer, M. (2010). Isoprenoid biosynthesis via the methylerythritol phosphate pathway: structural variations around phosphonate anchor and spacer of fosmidomycin, a potent inhibitor of deoxyxylulose phosphate reductoisomerase. The Journal of Organic Chemistry, 75(10), 3203-7. https://doi.org/10.1021/jo9024732
Zinglé C, et al. Isoprenoid Biosynthesis Via the Methylerythritol Phosphate Pathway: Structural Variations Around Phosphonate Anchor and Spacer of Fosmidomycin, a Potent Inhibitor of Deoxyxylulose Phosphate Reductoisomerase. J Org Chem. 2010 May 21;75(10):3203-7. PubMed PMID: 20429517.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isoprenoid biosynthesis via the methylerythritol phosphate pathway: structural variations around phosphonate anchor and spacer of fosmidomycin, a potent inhibitor of deoxyxylulose phosphate reductoisomerase. AU - Zinglé,Catherine, AU - Kuntz,Lionel, AU - Tritsch,Denis, AU - Grosdemange-Billiard,Catherine, AU - Rohmer,Michel, PY - 2010/5/1/entrez PY - 2010/5/1/pubmed PY - 2010/9/2/medline SP - 3203 EP - 7 JF - The Journal of organic chemistry JO - J Org Chem VL - 75 IS - 10 N2 - Fosmidomycin and its analogue FR-900098 are potent inhibitors of 1-deoxy-d-xylulose 5-phosphate reducto-isomerase (DXR), the second enzyme of the MEP pathway for the biosynthesis of isoprenoids. This paper describes the synthesis of analogues of the two reverse phosphonohydroxamic acids 3 and 4, in which the length of the carbon spacer is modified, the N-methyl group of 3 is replaced by an ethyl group, and the phosphate group is replaced by potential isosteric moieties, i.e., sulfonate or carboxylate functionalities. The potential of the synthesized analogues to inhibit the E. coli DXR was evaluated. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/20429517/Isoprenoid_biosynthesis_via_the_methylerythritol_phosphate_pathway:_structural_variations_around_phosphonate_anchor_and_spacer_of_fosmidomycin_a_potent_inhibitor_of_deoxyxylulose_phosphate_reductoisomerase_ L2 - https://doi.org/10.1021/jo9024732 DB - PRIME DP - Unbound Medicine ER -