title: Lithium-catalyzed hydroxide attack at the carbon atom of methyl phosphate.
abstract: The spontaneous hydrolysis of phosphate ester monoanions is relatively easy, but the reaction of water with simple phosphate ester dianion appears to be the slowest biomimetic reaction whose spontaneous rate has been measured in water, with an estimated half time of approximately 1012 years at room temperature in the absence of a catalyst. Here, we report an alternative mode of cleavage of methyl phosphate that involves hydroxide attack at the carbon atom of methyl phosphate and proceeds at a rate proportional to the square of the concentration of lithium hydroxide.
authors.affiliation: Department of Biochemistry & Biophysics, University of North Carolina, Chapel Hill, North Carolina 27599, USA. water@med.unc.edu
authors.forename: Richard
authors.initials: R
authors.lastname: Wolfenden
authors.forename: Frances
authors.initials: F
authors.lastname: Zhao
mesh_terms: D000838:Anions / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006878:Hydroxides / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D010755:Organophosphates / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*
chemical_list: D000838:Anions; D006878:Hydroxides; D010755:Organophosphates; D010710:Phosphates; D002244:Carbon; C027265:methylphosphate; D008094:Lithium