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

Catalog No.
C8679
A lipid biosynthesis intermediate
Grouped product items
SizePriceStock Qty
100mg
$80.00
Ship with 10-15 days
For scientific research use only and should not be used for diagnostic or medical purposes.

Tel: +1-832-696-8203

Email: [email protected]

Worldwide Distributors

Background

G3P is a pivotal metabolic intermediate linking glycolysis and lipid metabolism, endowed with multiple biological activities and functions. It participates in the glycerol phosphate shuttle, facilitating the transfer of NADH reducing equivalents to the oxidative phosphorylation pathway and regenerating NAD⁺. As a substrate in synthetic biology research on reactive oxygen species, G3P is utilized to assess its availability in cardiac tissues. Furthermore, it serves as a substrate for intracellular glycerol-3-phosphate acyltransferase, thereby influencing insulin production and playing a critical role in systemic acquired resistance in plants. Aberrant levels of G3P have also been associated with salivary alterations in patients with Alzheimer’s disease, frontotemporal dementia, and Lewy body dementia, underscoring its central role in lipid biosynthesis and the pathogenesis of various metabolic and neurodegenerative disorders.

References:

[1] Frasson D, Boschini RP, Chaves VE, dos Santos ME, Paula Gomes S, Valentim RR, Garófalo MA, Navegantes LC, Migliorini RH, Kettelhut Ido C. The sympathetic nervous system regulates the three glycerol-3P generation pathways in white adipose tissue of fasted, diabetic and high-protein diet-fed rats. Metabolism. 2012 Oct;61(10):1473-85. doi: 10.1016/j.metabol.2012.03.014. Epub 2012 May 15. PMID: 22592131.

[2] Cottingham IR, Ragan CI. Purification and properties of L-3-glycerophosphate dehydrogenase from pig brain mitochondria. Biochem J. 1980 Oct 15;192(1):9-18. doi: 10.1042/bj1920009. PMID: 6796038; PMCID: PMC1162302.

[3] Shen W, Wei Y, Dauk M, Tan Y, Taylor DC, Selvaraj G, Zou J. Involvement of a glycerol-3-phosphate dehydrogenase in modulating the NADH/NAD+ ratio provides evidence of a mitochondrial glycerol-3-phosphate shuttle in Arabidopsis. Plant Cell. 2006 Feb;18(2):422-41. doi: 10.1105/tpc.105.039750. Epub 2006 Jan 13. PMID: 16415206; PMCID: PMC1356549.

[4] Yeh JI, Chinte U, Du S. Structure of glycerol-3-phosphate dehydrogenase, an essential monotopic membrane enzyme involved in respiration and metabolism. Proc Natl Acad Sci U S A. 2008 Mar 4;105(9):3280-5. doi: 10.1073/pnas.0712331105. Epub 2008 Feb 22. PMID: 18296637; PMCID: PMC2265192.

[5] Mráček T, Drahota Z, Houštěk J. The function and the role of the mitochondrial glycerol-3-phosphate dehydrogenase in mammalian tissues. Biochim Biophys Acta. 2013 Mar;1827(3):401-10. doi: 10.1016/j.bbabio.2012.11.014. Epub 2012 Dec 7. PMID: 23220394.

[6] Scott A, Noga MJ, de Graaf P, Westerlaken I, Yildirim E, Danelon C. Cell-Free Phospholipid Biosynthesis by Gene-Encoded Enzymes Reconstituted in Liposomes. PLoS One. 2016 Oct 6;11(10):e0163058. doi: 10.1371/journal.pone.0163058. PMID: 27711229; PMCID: PMC5053487.

[7] Madungwe NB, Zilberstein NF, Feng Y, Bopassa JC. Critical role of mitochondrial ROS is dependent on their site of production on the electron transport chain in ischemic heart. Am J Cardiovasc Dis. 2016 Sep 15;6(3):93-108. PMID: 27679744; PMCID: PMC5030389.

[8] Morita SY, Ueda K, Kitagawa S. Enzymatic measurement of phosphatidic acid in cultured cells. J Lipid Res. 2009 Sep;50(9):1945-52. doi: 10.1194/jlr.D900014-JLR200. Epub 2009 Apr 15. PMID: 19369695; PMCID: PMC2724771.

[9] Yang Y, Zhao J, Liu P, Xing H, Li C, Wei G, Kang Z. Glycerol-3-phosphate metabolism in wheat contributes to systemic acquired resistance against Puccinia striiformis f. sp. tritici. PLoS One. 2013 Nov 29;8(11):e81756. doi: 10.1371/journal.pone.0081756. PMID: 24312351; PMCID: PMC3843702.

[10] Mugabo Y, Zhao S, Seifried A, Gezzar S, Al-Mass A, Zhang D, Lamontagne J, Attane C, Poursharifi P, Iglesias J, Joly E, Peyot ML, Gohla A, Madiraju SR, Prentki M. Identification of a mammalian glycerol-3-phosphate phosphatase: Role in metabolism and signaling in pancreatic β-cells and hepatocytes. Proc Natl Acad Sci U S A. 2016 Jan 26;113(4):E430-9. doi: 10.1073/pnas.1514375113. Epub 2016 Jan 11. PMID: 26755581; PMCID: PMC4743820.

[11] Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M. Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. PMID: 23857558.

Chemical Properties

StorageStore at -20°C
M.Wt370.43 (free acid)
FormulaC3H9O6P • 2C6H13N [XH2O]
SynonymsG3P
Chemical Name1,2R,3-propanetriol, 1-(dihydrogen phosphate), cyclohexanamine, hydrate (1:2:X)
SDFDownload SDF
Canonical SMILESOC[C@@H](O)COP(O)(O)=O.NC1CCCCC1.NC2CCCCC2.O
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

Quality Control

Quality Control & MSDS

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Chemical structure

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