Synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol and 2-C-methyl-D-erythritol-4-phosphate

Andrew T Koppisch, C. Dale Poulter

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

2-C-Methyl-D-erythritol 4-phosphate (MEP, 2) and 4-diphosphocytidyl-2-C-methyl-D-erythritol (CDPME, 3) are metabolites in the MEP pathway for biosynthesis of isoprenoid compounds in bacteria, plant chloroplasts, and algae. The free phosphoacid of 2 was prepared from benzyloxyacetone in five steps with an overall yield of 27% and an enantiomeric ratio (er) of 75:25. Following titration to the corresponding tributylammonium salt, 2 was coupled to cytidine 5'-monophosphate using a protocol originally developed for synthesis of base-sensitive nucleoside diphosphate sugars to give 3 in 40% yield, following purification by size exclusion chromatography.

Original languageEnglish (US)
Pages (from-to)5416-5418
Number of pages3
JournalJournal of Organic Chemistry
Volume67
Issue number15
DOIs
StatePublished - Jul 26 2002
Externally publishedYes

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Nucleoside Diphosphate Sugars
Erythritol
Cytidine
Size exclusion chromatography
Biosynthesis
Terpenes
Algae
Metabolites
Titration
Purification
Bacteria
Salts
2-C-methylerythritol 4-phosphate
2-methyl-1,2-epoxypropane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol and 2-C-methyl-D-erythritol-4-phosphate. / Koppisch, Andrew T; Poulter, C. Dale.

In: Journal of Organic Chemistry, Vol. 67, No. 15, 26.07.2002, p. 5416-5418.

Research output: Contribution to journalArticle

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abstract = "2-C-Methyl-D-erythritol 4-phosphate (MEP, 2) and 4-diphosphocytidyl-2-C-methyl-D-erythritol (CDPME, 3) are metabolites in the MEP pathway for biosynthesis of isoprenoid compounds in bacteria, plant chloroplasts, and algae. The free phosphoacid of 2 was prepared from benzyloxyacetone in five steps with an overall yield of 27{\%} and an enantiomeric ratio (er) of 75:25. Following titration to the corresponding tributylammonium salt, 2 was coupled to cytidine 5'-monophosphate using a protocol originally developed for synthesis of base-sensitive nucleoside diphosphate sugars to give 3 in 40{\%} yield, following purification by size exclusion chromatography.",
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