Biomaterial Database

Effect of racemic and S(+) alpha-chlorohydrin-1-phosphate on glyceraldehyde-3-phosphate dehydrogenase in relation to its contraceptive action. 1978

R W Fitzpatrick, and H Jackson, and N A Dickinson

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.

UI	MeSH Term	Description	Entries
D007535	Isomerases	A class of enzymes that catalyze geometric or structural changes within a molecule to form a single product. The reactions do not involve a net change in the concentrations of compounds other than the substrate and the product.(from Dorland, 28th ed) EC 5.	Isomerase
D008297	Male		Males
D009132	Muscles	Contractile tissue that produces movement in animals.	Muscle Tissue,Muscle,Muscle Tissues,Tissue, Muscle,Tissues, Muscle
D011817	Rabbits	A burrowing plant-eating mammal with hind limbs that are longer than its fore limbs. It belongs to the family Leporidae of the order Lagomorpha, and in contrast to hares, possesses 22 instead of 24 pairs of chromosomes.	Belgian Hare,New Zealand Rabbit,New Zealand Rabbits,New Zealand White Rabbit,Rabbit,Rabbit, Domestic,Chinchilla Rabbits,NZW Rabbits,New Zealand White Rabbits,Oryctolagus cuniculus,Chinchilla Rabbit,Domestic Rabbit,Domestic Rabbits,Hare, Belgian,NZW Rabbit,Rabbit, Chinchilla,Rabbit, NZW,Rabbit, New Zealand,Rabbits, Chinchilla,Rabbits, Domestic,Rabbits, NZW,Rabbits, New Zealand,Zealand Rabbit, New,Zealand Rabbits, New,cuniculus, Oryctolagus
D002728	Chlorohydrins	Any of the compounds derived from a group of glycols or polyhydroxy alcohols by chlorine substitution for part of the hydroxyl groups. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Chlorhydrins
D003272	Contraceptive Agents, Male	Chemical substances or agents with contraceptive activity in males. Use for male contraceptive agents in general or for which there is no specific heading.	Male Contraceptive,Contraceptives, Male,Agents, Male Contraceptive,Contraceptive, Male,Male Contraceptive Agents,Male Contraceptives
D005987	Glyceraldehyde-3-Phosphate Dehydrogenases	Enzymes that catalyze the dehydrogenation of GLYCERALDEHYDE 3-PHOSPHATE. Several types of glyceraldehyde-3-phosphate-dehydrogenase exist including phosphorylating and non-phosphorylating varieties and ones that transfer hydrogen to NADP and ones that transfer hydrogen to NAD.	GAPD,Glyceraldehyde-3-Phosphate Dehydrogenase,Glyceraldehydephosphate Dehydrogenase,Phosphoglyceraldehyde Dehydrogenase,Triosephosphate Dehydrogenase,Dehydrogenase, Glyceraldehyde-3-Phosphate,Dehydrogenase, Glyceraldehydephosphate,Dehydrogenase, Phosphoglyceraldehyde,Dehydrogenase, Triosephosphate,Dehydrogenases, Glyceraldehyde-3-Phosphate,Glyceraldehyde 3 Phosphate Dehydrogenase
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D019998	Racemases and Epimerases	Enzymes that catalyze inversion of the configuration around an asymmetric carbon in a substrate having one (racemase) or more (epimerase) center(s) of asymmetry. (Dorland, 28th ed) EC 5.1.	Epimerase,Epimerases,Racemase,Racemases,Epimerases and Racemases