sn-Glycerol-3-phosphate (cyclohexyl ammonium salt hydrate)

sn-Glycerol-3-phosphate (G3P) is a phosphoric ester of glycerol that is a chemical intermediate in glycolysis and lipid metabolism.¹ G3P is an integral part of the glycerophosphate shuttle, in which NADH is oxidized to regenerate NAD⁺ and reducing equivalents are transferred to the oxidative phosphorylation pathway.^2,3,4,5 G3P is used as a substrate for lipid biosynthesis pathways in synthetic biology, in studies of reactive oxygen species in heart tissue, and to measure phosphatidic acid in cell cultures.^6,7,8 It plays a vital role in systemic acquired resistance in plant immunity.⁹ G3P availability affects insulin production as a substrate for glycerol-3-phosphate phosphatase.¹⁰ Altered levels of G3P have been found in the saliva of Alzheimer's, frontal lobe dementia, and Lewy body disease patients.¹¹

1.Frasson, D., Boschini, R.P., Chaves, V.E., et al.The sympathetic nervous system regulates the three glycerol-3P generation pathways in white adipose tissue of fasted, diabetic and high-protein diet-fed ratsMetabolism61(10)1473-1485(2012) 2.Cottingham, I.R., and Ragan, C.I.Purification and properties of L-3-glycerophosphate dehydrogenase from pig brain mitochondriaBiochem J.192(1)9-18(1980) 3.Shen, W., Wei, Y., Dauk, M., et al.Involvement of a glycerol-3-phosphate dehydrogenase in modulating the NADH/NAD+ ratio provides evidence of a mitochondrial glycerol-3-phosphate shuttle in ArabidopsisPlant Cell18(2)422-441(2006) 4.Yeh, J.I., Chinte, U., and Du, S.J.Structure of glycerol-3-phosphate dehydrogenase, an essential monotopic membrane enzyme involved in respiration and metabolismProc. Natl. Acad. Sci. USA105(9)3280-3285(2008) 5.MrÁ?ek, T., Drahota, Z., and Houštěk, J.The function and the role of the mitochondrial glycerol-3-phosphate dehydrogenase in mammalian tissuesBiochim Biophys. Acta.1827(3)401-410(2013) 6.Scott, A., Noga, M.J., De Graaf, P.T., et al.Cell-free phospholipid biosynthesis by gene-encoded enzymes reconstituted in liposomesPLoS One11(10)e0163058(2016) 7.Madungwe, N., Zilberstein, N.F., Feng, Y., et al.Critical role of mitochondrial ROS is dependent on their site of production on the electron transport chain in ischemic heartAm. J. Cardiovasc. Dis.6(3)93-108(2016) 8.Morita, S.y., Ueda, K., and Kitagawa, S.Enzymatic measurement of phosphatidic acid in cultured cellsJ. Lipid Res.50(9)1945-1952(2009) 9.Yang, Y., Zhao, J., Liu, P., et al.Glycerol-3-phosphate metabolism in wheat contributes to systemic acquired resistance against Puccinia striiformis f. sp. triticiPLoS One8(11)e81756(2013) 10.Mugabo, Y., Zhao, S., Seifried, A., et al.Identification of a mammalian glycerol-3-phosphate phosphatase: Role in metabolism and signaling in pancreatic β-cells and hepatocytesProc. Natl. Acad. Sci. USAE430-439(2016) 11.Tsuruoka, M., Hara, J., Hirayama, A., et al.Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patientsElectrophoresis34(19)2865-2872(2013)