Formal synthesis of 4-diphosphocytidyl-2-C-methyl d-erythritol from d-(+)-arabitol

2-C-Methyl-d-erythritol-4-phosphate (MEP) is a key chemical intermediate of the non-mevalonate pathway for isoprenoid biosynthesis employed by many pathogenic microbes. MEP is also the precursor for the synthesis of 4-diphosphocytidyl-2-C-methyl d-erythritol (CDP-ME), another key intermediate of the...

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Bibliographic Details
Published in:Tetrahedron 2012-10, Vol.68 (43), p.8937-8941
Main Authors: Odejinmi, Sina I., Rascon, Rafael G., Chen, Wyman, Lai, Kent
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiinfectives and antibacterials
Bioconversions. Hemisynthesis
Biological and medical sciences
Biosynthesis
Biotechnology
CDP-ME
Chemistry
Dioxanone
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
General aspects
Human
Medical sciences
MEP
Methods. Procedures. Technologies
Microorganisms
Monophosphate
Organic chemistry
Organometalloidal and organometallic compounds
P derivatives
Pathways
Pharmacology. Drug treatments
Precursors
Preparations and properties
Selective phosphorylation
Synthesis
Tetrahedrons
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Summary:2-C-Methyl-d-erythritol-4-phosphate (MEP) is a key chemical intermediate of the non-mevalonate pathway for isoprenoid biosynthesis employed by many pathogenic microbes. MEP is also the precursor for the synthesis of 4-diphosphocytidyl-2-C-methyl d-erythritol (CDP-ME), another key intermediate of the non-mevalonate pathway. As this pathway is non-existent in higher animals, including humans, it represents great opportunities for novel antimicrobial development. To facilitate the in-depth studies of this pathway, we reported here a formal synthesis of CDP-ME through a new synthesis of 2-C-methyl-d-erythritol-4-phosphoric acid from d-(+)-arabitol. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.08.020