N-methylimidazolium chloride-catalyzed pyrophosphate formation: application to the synthesis of Lipid I and NDP-sugar donors |
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Authors: | Tsukamoto Hirokazu Kahne Daniel |
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Affiliation: | Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, United States |
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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. 31P 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. |
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Keywords: | N-Methylimidazolium chloride Pyrophosphate formation Phosphorimidazolide Phosphoromorpholidate Lipid I NDP-sugar donors |
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