Synthesis of Methoxycarbonyl Phosphate, a New Reagent Having High Phosphoryl Donor Potential for Use in ATP Cofactor Regeneration

Romas J. Kazlauskas, George M. Whitesides

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

Reaction of an aqueous solution of phosphate ion (pH 7.8) with acetic anhydride in a two-phase system gives acetyl phosphate. Reaction of phosphate with methyl chloroformate yields methoxycarbonyl phosphate. Both reagents are useful for in situ regeneration of ATP from ADP in organic synthetic procedures based on enzyme-catalyzed reactions requiring ATP. Acetyl phosphate has been used for this purpose previously; methoxycarbonyl phosphate is a new compound, and its use in ATP regeneration is also new. The characteristics of methoxycarbonyl phosphate which makes it interesting are its ease of preparation, its acceptability as a substrate for both acetate kinase and carbamate kinase, and its high phosphoryl donor potential. It has the additional attractive feature that the product remaining after phosphoryl transfer, methyl carbonate, decomposes spontaneously in solution and forms methanol and carbon dioxide. These products present no difficulties in workup and avoid the problem of product inhibition which is sometimes troublesome in regeneration schemes based on acetyl phosphate or phosphoenolpyruvate. The principal disadvantage of methoxycarbonyl phosphate as a phosphorylating reagent in ATP regeneration, relative to acetyl phosphate, is that it decomposes inconveniently rapidly under the conditions used for enzymatic synthesis (t1/2=0.3 h at 25 °C, pH 7).

Original languageEnglish (US)
Pages (from-to)1069-1076
Number of pages8
JournalJournal of Organic Chemistry
Volume50
Issue number7
DOIs
StatePublished - Apr 1985

Fingerprint Dive into the research topics of 'Synthesis of Methoxycarbonyl Phosphate, a New Reagent Having High Phosphoryl Donor Potential for Use in ATP Cofactor Regeneration'. Together they form a unique fingerprint.

  • Cite this