Protein Information

Name glyceraldehyde 3 phosphate dehydrogenase
Synonyms CDABP0047; G3PD; GAPD; GAPD protein; GAPDH; Glyceraldehyde 3 phosphate dehydrogenase; GAPD proteins; Glyceraldehyde 3 phosphate dehydrogenases

Compound Information

Name α-chlorohydrin
CAS 3-chloro-1,2-propanediol

Reference List

PubMed Abstract RScore(About this table)
16322075 Nemeti B, Csanaky I, Gregus Z: Effect of an inactivator of glyceraldehyde-3-phosphate dehydrogenase, a fortuitous arsenate reductase, on disposition of arsenate in rats. Toxicol Sci. 2006 Mar;90(1):49-60. Epub 2005 Dec 1.

7(0,0,0,7) Details
6887131 Ford WC, Harrison A: The activity of glyceraldehyde 3-phosphate dehydrogenase in spermatozoa from different regions of the epididymis in laboratory rodents treated with alpha-chlorohydrin or 6-chloro-deoxyglucose. J Reprod Fertil. 1983 Sep;69(1):147-56.

6(0,0,0,6) Details
19542219 Frayne J, Taylor A, Cameron G, Hadfield AT: Structure of insoluble rat sperm glyceraldehyde-3-phosphate dehydrogenase (GAPDH) via heterotetramer formation with Escherichia coli GAPDH reveals target for contraceptive design. J Biol Chem. 2009 Aug 21;284(34):22703-12. Epub 2009 Jun 19.

5(0,0,0,5) Details
4020765 Stevenson D, Jones AR: Production of (S)-3-chlorolactaldehyde from (S)-alpha-chlorohydrin by boar spermatozoa and the inhibition of glyceraldehyde 3-phosphate dehydrogenase in vitro. J Reprod Fertil. 1985 May;74(1):157-65.

3(0,0,0,3) Details
9702787 Sheline CT, Choi DW: Neuronal death in cultured murine cortical cells is induced by inhibition of GAPDH and triosephosphate isomerase. Neurobiol Dis. 1998 Jul;5(1):47-54.

3(0,0,0,3) Details
6673906 Ford SA, Jones AR: The effect of alpha-chlorohydrin on the oxidation of fructose by rabbit spermatozoa in vitro. Contraception. 1983 Dec;28(6):565-73.


At a concentration of 50 mM, (R,S)-alpha-chlorohydrin causes the specific inhibition of the enzyme glyceraldehyde 3-phosphate dehydrogenase and is metabolised by the spermatozoa to 3-chlorolactaldehyde of unknown configuration.
2(0,0,0,2) Details
6776277 Ford WC, Harrison A: Effect of alpha-chlorohydrin on glucose metabolism by spermatozoa from the cauda epididymidis of the rhesus monkey (Macaca mulatta). J Reprod Fertil. 1980 Sep;60(1):59-64.


It was concluded that the activity of glyceraldehyde 3-phosphate dehydrogenase (EC 1.2.1.12) limited flux through the glycolytic pathway.
2(0,0,0,2) Details
11012786 Bone W, Cooper TG: In vitro inhibition of rat cauda epididymal sperm glycolytic enzymes by ornidazole, alpha-chlorohydrin and 1-chloro-3-hydroxypropanone. Int J Androl. 2000 Oct;23(5):284-93.


The dose-dependent inhibition in vitro of the glycolytic enzymes glyceraldehyde-3-phosphate dehydrogenase (GAPDH) and triosephosphate isomerase (TPI) of distal cauda epididymal rat spermatozoa by (R)-, (S)- and (R,S)-ornidazole (ORN), (R,S)-alpha-chlorohydrin (ACH) and 1-chloro-3-hydroxypropanone (CHOP) was compared.
2(0,0,0,2) Details
11399799 Jelks KB, Miller MG: alpha-Chlorohydrin inhibits glyceraldehyde-3-phosphate dehydrogenase in multiple organs as well as in sperm. Toxicol Sci. 2001 Jul;62(1):115-23.

2(0,0,0,2) Details
729374 Fitzpatrick RW, Jackson H, Dickinson NA: Effect of racemic and S (+) alpha-chlorohydrin-1-phosphate on glyceraldehyde-3-phosphate dehydrogenase in relation to its contraceptive action. Contraception. 1978 Nov;18(5):477-83.

2(0,0,0,2) Details
629780 Brown-Woodman PD, Mohri H, Mohri T, Suter D, White IG: Mode of action of alpha-chlorohydrin as a male anti-fertility agent. Biochem J. 1978 Jan 15;170(1):23-37.


After incubation with 3mm-alpha-chlorohydrin, glyceraldehyde 3-phosphate dehydrogenase and triose phosphate isomerase activities were decreased by approx. 90% and 80% respectively, and in some experiments aldolase was also inhibited.
2(0,0,0,2) Details
6861971 Jones AR, Stevenson D: Formation of the active antifertility metabolite of (S)-alpha-chlorohydrin in boar sperm. Experientia. 1983 Jul 15;39(7):784-5.


The presence of glycerol decreases the activity of this enzyme towards (S)-alpha-chlorohydrin in vitro thereby preventing the formation of (S)-3-chlorolactaldehyde, an inhibitor of glyceraldehyde 3-phosphate dehydrogenase in boar sperm.
1(0,0,0,1) Details
16407453 Ford WC: Glycolysis and sperm motility: does a spoonful of sugar help the flagellum go round?. Hum Reprod Update. 2006 May-Jun;12(3):269-74. Epub 2006 Jan 11.


An obligatory role for glycolysis is supported by the lack of progressive motility in sperm from mice where the gene for sperm-specific glyceraldehyde-3-phosphate dehydrogenase (GAPDHs) had been 'knocked out'.
1(0,0,0,1) Details
8848575 Jones AR, Porter LM: Inhibition of glycolysis in boar spermatozoa by alpha-chlorohydrin phosphate appears to be mediated by phosphatase activity. Reprod Fertil Dev. 1995;7(5):1089-94.


The high phosphatase activity hydrolyses the ester to alpha-chlorohydrin which undergoes oxidation to (S)-3-chlorolactaldehyde, a specific inhibitor of sperm glyceraldehyde-3-phosphate dehydrogenase and triosephosphate isomerase, thereby exhibiting an anti-glycolytic action.
1(0,0,0,1) Details
21325689 Terrell KA, Wildt DE, Anthony NM, Bavister BD, Leibo SP, Penfold LM, Marker LL, Crosier AE: Glycolytic enzyme activity is essential for domestic cat (Felis catus) and cheetah (Acinonyx jubatus) sperm motility and viability in a sugar-free medium. Biol Reprod. 2011 Jun;84(6):1198-206. Epub 2011 Feb 16.


A second set of ejaculates was exposed to a chemical inhibitor of either lactate dehydrogenase (sodium oxamate) or glyceraldehyde-3-phosphate dehydrogenase (alpha-chlorohydrin).
1(0,0,0,1) Details
11330647 Bone W, Jones AR, Morin C, Nieschlag E, Cooper TG: Susceptibility of glycolytic enzyme activity and motility of spermatozoa from rat, mouse, and human to inhibition by proven and putative chlorinated antifertility compounds in vitro. J Androl. 2001 May-Jun;22(3):464-70.


A dose-dependent inhibition of the glycolytic enzyme, glyceraldehyde 3-phosphate dehydrogenase (GAPDH), of rat and mouse distal cauda epididymidal and human ejaculated sperm by ACH, CHOP, and DCDF was demonstrated.
1(0,0,0,1) Details
20409345 Xie S, Zhu Y, Ma L, Lu Y, Zhou J, Gui Y, Cao L: Genome-wide profiling of gene expression in the epididymis of alpha-chlorohydrin-induced infertile rats using an oligonucleotide microarray. Reprod Biol Endocrinol. 2010 Apr 22;8:37.


BACKGROUND: As one of the chlorinated antifertility compounds, alpha-chlorohydrin (ACH) can inhibit glyceraldehyde-3-phosphate dehydrogenase (G3PDH) activity in epididymal sperm and affect sperm energy metabolism, maturation and fertilization, eventually leading to male infertility.
1(0,0,0,1) Details
17321661 Skamarauskas J, Carter W, Fowler M, Madjd A, Lister T, Mavroudis G, Ray DE: The selective neurotoxicity produced by 3-chloropropanediol in the rat is not a result of energy deprivation. Toxicology. 2007 Apr 11;232(3):268-76. Epub 2007 Jan 21.


The biochemical mechanism of toxicity of the experimental astrocyte neurotoxicant and food contaminant S-3-chloro-1,2-propanediol (3-CPD) has been proposed to be via inhibition of glyceraldehyde-3-phosphate dehydrogenase (GAPDH).
1(0,0,0,1) Details
6715067 Stevenson D, Jones AR: The action of (R)- and (S)-alpha-chlorohydrin and their metabolites on the metabolism of boar sperm. Int J Androl. 1984 Feb;7(1):79-86.


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.
1(0,0,0,1) Details
483861 Jones AR, Mashford PM, Murcott C: The metabolism of 3-amino-1-chloropropan-2-ol in relation to its antifertility activity in male rats. Xenobiotica. 1979 Apr;9(4):253-61.


A difference in metabolic rate or route of the isomers may account for their differing physiological activities. 4. (+)- and (-)-aminochloropropanol exhibited identical in vitro inhibitory activities on the glycolytic enzymes glyceraldehyde-3-phosphate dehydrogenase and triosephosphate isomerase, and were substrates for monoamine oxidase to equivalent extents.
1(0,0,0,1) Details
7277334 Ford WC, Harrison A, Waites GM: Effects of 6-chloro-6-deoxysugars on glucose oxidation in rat spermatozoa. . J Reprod Fertil. 1981 Sep;63(1):67-73.


Glucose oxidation appeared to be inhibited at the triose phosphate isomerase or glyceraldehyde 3-phosphate dehydrogenase reaction.
1(0,0,0,1) Details
3593119 Jones AR, Bubb WA, Murdoch SR, Stevenson DA: Inhibition of fructolytic enzymes in boar spermatozoa by (S)-alpha-chlorohydrin and 1-chloro-3-hydroxypropanone. Aust J Biol Sci. 1986;39(4):395-406.


When boar spermatozoa were incubated with the (S)-isomer of the male antifertility agent alpha-chlorohydrin the activity of glyceraldehyde-3-phosphate dehydrogenase was inhibited.
1(0,0,0,1) Details
7471740 Hutton P, Dawson AG, Jones AR: Inhibition of glycolysis in boar sperm by alpha-chlorohydrin. Contraception. 1980 Nov;22(5):505-12.


Low levels of alpha-chlorohydrin increased the cellular concentrations of fructose-1,6-bisphosphate and the triosephosphates, an effect consistent with the inhibition of glyceraldehyde-3-phosphate dehydrogenase.
1(0,0,0,1) Details
563260 Dickinson NA, Fitzpatrick RW, Jackson H: Antifertility mode of action of alpha-chlorohydrin--interaction with glyceraldehyde-3-phosphate-dehydrogenase [proceedings]. Br J Pharmacol. 1977 Nov;61(3):456P.

1(0,0,0,1) Details
3339589 Cooney SJ, Jones AR: Inhibitory effects of (S)-3-chlorolactaldehyde on the metabolic activity of boar spermatozoa in vitro. J Reprod Fertil. 1988 Jan;82(1):309-17.


(S)-alpha-Chlorohydrin and 3-chloro-1-hydroxyacetone inhibited the oxidative metabolism of fructose by boar spermatozoa only after a period of incubation in which they presumably underwent conversion to (S)-3-chlorolactaldehyde, an inhibitor of sperm glyceraldehyde 3-phosphate dehydrogenase.
1(0,0,0,1) Details