Effect of racemic and S(+) alpha-chlorohydrin-1-phosphate on glyceraldehyde-3-phosphate dehydrogenase in relation to its contraceptive action.
The phosphate esters of racemic (+/-) alpha-chlorohydrin and its S(+)-optical isomer have been prepared as cyclohexylamine salts. In vitro both inhibited glyceraldehyde-3-phosphate dehydrogenase by a competitive mechanism, whereas (+/-) alpha-chlorohydrin did not. The S(+)-isomer was approximately four times as potent as the racemate. These results correlate with data concerning the relative contraceptive activity in rats of racemic and S(+) alpha-chlorohydrin. They support the view that the antifertility mechanism involves in vivo formation of S(+) alpha-chlorohydrin-1-phosphate, with resulting inhibition of glycolysis in sperm.
D000818:Animals; D002728:Chlorohydrins / Q000494:pharmacology*; D003272:Contraceptive Agents, Male / Q000494:pharmacology*; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases / Q000378:metabolism*; D007535:Isomerases / Q000494:pharmacology*; D008297:Male; D009132:Muscles / Q000201:enzymology; D011817:Rabbits; D019998:Racemases and Epimerases / Q000494:pharmacology*; D013237:Stereoisomerism
D002728:Chlorohydrins; D003272:Contraceptive Agents, Male; D005987:Glyceraldehyde-3-Phosphate Dehydrogenases; D007535:Isomerases; D019998:Racemases and Epimerases