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Bioorg Med Chem Lett. 2011 Sep 1;21(17):5050-3. doi: 10.1016/j.bmcl.2011.04.061. Epub 2011 Apr 22.

N-methylimidazolium chloride-catalyzed pyrophosphate formation: application to the synthesis of Lipid I and NDP-sugar donors.

Author information

1
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, United States.

Abstract

N-Methylimidazolium chloride is found to catalyze a coupling reaction between monophosphates and activated phosphorous-nitrogen intermediates such as a phosphorimidazolide and phosphoromorpholidate to form biologically important unsymmetrical pyrophosphate diesters. The catalyst is much more active, cheaper, and less explosive than 1H-tetrazole, known as the best catalyst for the pyrophosphate formation over a decade. The mild and neutral reaction conditions are compatible with allylic pyrophosphate formation in Lipid I syntheisis. (31)P NMR experiments suggest that the catalyst acts not only as an acid but also as a nucleophile to form cationic and electrophilic phosphor-N-methylimidazolide intermediates in the pyrophosphate formation.

PMID:
21592792
PMCID:
PMC3156252
DOI:
10.1016/j.bmcl.2011.04.061
[Indexed for MEDLINE]
Free PMC Article

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