Abstract
2,3-Diphosphono-DL-glyceric acid, a racemic phosphonic acid, analogue of 2,3-diphospho-D-glyceric acid, the cofactor of phosphoglyceric acid mutase and hemoglobin, has been synthesized. It was obtained by treating the methyl esters of either β-chlorolactic acid, β-bromolactic acid, or glyceric acid with triethyl phosphite at 140–145° for 48 h, hydrolyzing the major reaction product tetraethyl 2,3-diphosphono-DL-glyceric acid methyl ester with concentrated hydrobromic acid at 140° for 24 h, and isolating 2,3-diphosphono-DL-glyceric acid as pentabarium or tricyclohexylammonium salt. 2,3-Diphosphonoglyceric acid and 2,3-diphosphoglyceric acid are readily distinguished from each other by chromatographic and chemical as well as by spectroscopic methods.
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