Absolute configuration of tritiated O-alkylglycerol synthesized enzymatically from (1,3-3H2,...

O-Alkyldihydroxyacetone phosphate is synthesized enzymatically from hexadecanol and acyldihydroxyacetone phosphate. In this process there is a hydrogen exchange in which the pro-R hydrogen of C-1 of the sn-glycerol moiety is lost. This hydrogen is replaced by a hydrogen from the medium. In order to obtain additional information on the mechanism of ether bond formation, it would be of interest to know whether or not the hydrogen exchange results in a change of configuration in the product, O-alkyldihydroxyacetone phosphate. By using O-alkylglycerol prepared both chemically and enzymatically from isomerase-treated [1,3-3H2, 1,3-14C2] dihydroxyacetone phosphate and an O-alkylglycerol cleavage enzyme system, it was shown that the hydrogen exchange occurs with retention of configuration of the substituents of C-1 of the sn-glycerol moiety.