S-(+)-3,4-Dihydroxybutylphosphonic acid, an isosteric analogue of sn-glycerol 3-phosphate, was synthesized stereospecifically and shown to be an effective substrate for rabbit muscle glycerol 3-phosphate dehydrogenase (sn-glycerol 3-phosphate–NAD+oxidoreductase, EC 1.1.1.8). Non-isosteric phosphonate analogues of sn-glycerol 3-phosphate showed neither substrate nor inhibitory activity with the enzyme.
