Dicarboxylic acid bis(methyl phosphates): anionic biomimetic crosslinking reagents

Abstract

Monoesters of acyl phosphates are anionic electrophiles and their difunctional analogues are expected to function as site-directed cross-linking reagents. Dimethyl phosphate anhydrides of mono- and dicarboxylic acids are conveniently prepared by the reaction of an acyl chloride with sodium dimethyl phosphate in tetrahydrofuran. These are converted to monomethyl acyl phosphates by reaction with sodium iodide. Methyl acetyl phosphate and a representative group of symmetrical difunctional bis(methyl phosphates) were prepared by this route. Hemoglobin is cross-linked in its reactions with difunctional methyl acyl phosphates