E. Baer, R. Robinson
Mar 1, 1971
Citations
0
Influential Citations
2
Citations
Journal
Canadian journal of biochemistry
Abstract
BAER, E., AND ROBM~N, R. Synthesis of 2;3-diphosphono-DL-glyceric acid, a racernic analogue of 2,3-diphosph*~-gjycekic acid. the cofactor sf both phosphoglyceric acid mutase and hemoglobin. Can. J. Biochem. 49,300-365 (1971). 2,3-Diphosphono-DL-g1yceric acid, a racernic phosphonic acid, analogue of 2,3=dighospho-~=glyceric acid, the cofactor of phssphoglyceric acid rnutase and hemoglobin, has ken synthesized. It was obtained by treating the methyl esters of either p-chlorolactic acid, /3-bromolactic acid, or glyceric acid with triethyl phosphite at 14@-145" for 48 h, hydrolyzing the major reaction product tetraethyl 2,s-diphosghono-DLgIyceric acid methyl ester with concentrated hydrsbrornic acid at f 48" for 24 h, and isolating 2,3-diphosphono-DL-glyceric acid as gentabarium or tricyclaal%exylammonium salt. 2,3-Diphosphonoglyceric wid and 2,3-diphosphoglyceric add are readily distinguished from each other by chromatographic and chemical as well as by spectroscopic methods. BAER, E., BT ROS~SON, W. Synthesis of 2,3-diphosphano-DL-glyceric acid, a racemic analogue of 2,3-&tiphospho-~-g1yceric acid, the cnfactor of both phosphoglyceric acid mutase and hemoglobin. Can. J. Biochem. 49,3W-30% (1 941). L'acide %,3-diphosphono-DL-glycbiqaae, un analogue acide phosphonique rackrnique de l'acide 2,3diphospho-D-glyckrique et le cofacteur de la phospboglyckromutase et de I'hkmoglobine, a CtC synthCtisk. Ce cornpod a CtC obtenu en traitant l'ester mkthylique de l'acide &chlarolactique, Qe 19spcide B-bromolwtique, su de B'acide glydrique par le trikthyl phosphite & 140-145" pendant 48 h, puis en hydrolysant le prodbait majeur de la rdwtion, B9ester rnkthylique de 19acide tCtraCthyl 2,3-diphosphono-DL-glycbrique, au moyen de 4'acide hydrobrorniq~e concentrd, A 140' pendant 24 h. L'acicide 2,3-diphosphono-DLglyc6rique a kt6 isole sous forme de sel de pentabariaam ou de tricyclohewylaammonium. L'acide 2,3diphosphonoglycCriqple se distingue fasilement de I'acide 2,3-diphosphogBycCrique par des rnkthodes cbsmataagaphique, chimique, et spectrompique. In&odaction In 1949, almost a quarter sf a century after In 1925, Greenwald (1) isolated from the erythrocytes of dog and pig blood an unknown organic phosphate which he identified as the 2,3-diphosphoric acid ester sf koo-rotatory glyceric acid (2,3=DPGA).%Although most tissues contain little of this compounds in mammalian erythrocytes 2,3-DPGA constitutes as much as half of the cellular organic phosphate (2). In 1958 Baer (3) reported the chemical synthesis of 2,3diphospho-~mglyceric acid, confirming the structure proposed by Greenwald for the natural compound, establishing unambiguously its csrafiguration (D), and thus its steresehemical relationship to the various intermediates of fermentation sand glycolysis.