Synthesis of 4-Diphosphocytidyl-2-C-methyl-d-erythritol and 2-C-Methyl-d-erythritol-4-phosphate
- 22 June 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (15) , 5416-5418
- https://doi.org/10.1021/jo025736o
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.Keywords
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