SYNTHESIS OF THE d( +)-a-GLYCEROPHOSPHORIC ACID AND THE ACTION OF PHOSPHATASES ON SYNTHETIC

The synthesis of the racemic a-glycerophosphoric acid (1) and of the I( -)-cr-glycerophosphoric acid (2) has been reported. The Z( -)-CL-glycerophosphoric acid has been isolated from various natural sources, such as phosphatides, and as an intermediate product of fermentation or glycolysis. For this reason, in a previous paper we called the I( -)-cr-glycerophosphoric acid the “biological” acid. The d( +)-Lu-glycerophosphoric acid has not yet been found in nature. We have carried out its synthesis in the same way as that of its optical antipode, and describe in this paper its preparation in the form of the barium salt and silver salt. The diethyl ether diethyl ester possessed in homogeneous substance the rotation [cx]~’ = +5.94“; in absolute ethyl alcohol [& = +6.69”. The principle of the synthesis, in which Z(-)acetone glycerol (3) is used as starting material is given in the accompanying formula which also explains the configurational relationship between d(+)-CC-glycerophosphoric acid and Z-glyceraldehyde. This method of synthesis of the cr-glycerophosphoric acids not only gives products of known configuration, but also produces the enantiomorphs in optically pure form, thus having an obvious advantage over previous methods (5, 6) which relied on resolution of the racemic acid. Since in many cases the deciding factor for the biological utilizability of substances with an asymmetrical carbon atom, such as