title: The action of (R)- and (S)-alpha-chlorohydrin and their metabolites on the metabolism of boar sperm.
abstract: The action of (R,S)-alpha-chlorohydrin in inhibiting glycolysis in boar sperm is due to the (S)-isomer. Its effect on the concentrations of glycolytic intermediates suggests that the pathway is inhibited at the glyceraldehyde 3-phosphate dehydrogenase reaction. alpha-Chlorohydrin is oxidized by boar liver homogenates via 3-chlorolactaldehyde to 3-chlorolactate. Racemic mixtures of both compounds, and a proposed metabolite, 3-chloropyruvate, inhibit the oxidative metabolism of fructose, lactate and pyruvate possibly by interfering with processes occurring within the sperm mitochondria. It is proposed that the toxic action of these metabolites account for the effects of (R)-alpha-chlorohydrin on sperm motility, as this compound possesses no antifertility activity of itself.
mesh_terms: D000818:Animals; D002728:Chlorohydrins / Q000494:pharmacology*; D006019:Glycolysis / Q000187:drug effects; D007536:Isomerism; D008297:Male; D013094:Spermatozoa / Q000187:drug effects / Q000378:metabolism*; D013552:Swine; D000517:alpha-Chlorohydrin / Q000494:pharmacology*
chemical_list: D002728:Chlorohydrins; D000517:alpha-Chlorohydrin