Summary
The male antifertility agent (S)-α-chlorohydrin (I) is metabolized by boar sperm to (S)-3-chlorolactaldehyde (II) by an enzyme that is involved in the oxidation of glycerol to glyceraldehyde. The presence of glycerol decreases the activity of this enzyme towards (S)-α-chlorohydrin in vitro thereby preventing the formation of (S)-3-chlorolactaldehyde, an inhibitor of glyceraldehyde 3-phosphate dehydrogenase in boar sperm.
References
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In a previous paper5 the incorrect stereochemical prefix was assigned to this metabolite.
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This work was supported by an Aboriginal Study Grant and the National Health and Medical Research Council of Australia.
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Jones, A.R., Stevenson, D. Formation of the active antifertility metabolite of (S)-α-chlorohydrin in boar sperm. Experientia 39, 784–785 (1983). https://doi.org/10.1007/BF01990326
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DOI: https://doi.org/10.1007/BF01990326