Synthesis of 4-diphosphocytidyl-2-C-methyl-D-erythritol and 2-C-methyl-D-erythritol-4-phosphate.
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.
Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA.
Andrew T
AT
Koppisch
C Dale
CD
Poulter
D001419:Bacteria / Q000378:metabolism; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D002736:Chloroplasts / Q000201:enzymology / Q000378:metabolism; D002853:Chromatography, Liquid; D004896:Erythritol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism; D056890:Eukaryota / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000378:metabolism*; D010944:Plants / Q000378:metabolism; D013403:Sugar Phosphates / Q000138:chemical synthesis*; D013559:Symbiosis
C114232:2-C-methylerythritol 4-phosphate; C400182:4-diphosphocytidyl-2-C-methylerythritol; D009943:Organophosphorus Compounds; D013403:Sugar Phosphates; D004896:Erythritol