Glycerol 1-phosphate

sn-Glycerol 1-phosphate
Names
	IUPAC name (2S)-2,3-dihydroxypropan-1-yl dihydrogen phosphate
	Other names (S)-2,3-dihydroxypropyl dihydrogen phosphate; 1,2,3-propanetriol, 1-(dihydrogen phosphate), (2S)-; L-glycerol 1-phosphate; D-glycerol 3-phosphate; D-α-glycerophosphate; D-α-phosphoglycerol
Identifiers
CAS Number	5746-57-6 ;
3D model (JSmol)	Interactive image;
MeSH	Alpha-glycerophosphoric+acid
PubChem CID	439276;
UNII	196623779E ;
	SMILES C([C@@H](COP(=O)(O)O)O)O;
Properties
Chemical formula	C3H9O6P
Molar mass	172.073 g·mol−1
Related compounds
Related organophosphates	Glycerol 2-phosphate; Glycerol 3-phosphate
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

sn-Glycerol 1-phosphate[1] is a phosphoric ester of glycerol, which is a component of archea-specific ether lipids. Equally appropriate names in biochemical context include glycero-1-phosphate, 1-O-phosphonoglycerol, and 1-phosphoglycerol.[2] From a historical reason, it is also known as L-glycerol 1-phosphate, D-glycerol 3-phosphate, and D-α-glycerophosphoric acid.[2]

Biosynthesis and metabolism

Glycerol 1-phosphate is synthesized by reducing dihydroxyacetone phosphate (DHAP), a glycolysis intermediate, with sn-glycerol-1-phosphate dehydrogenase.[3] DHAP and thus glycerol 1-phosphate is also possible to be synthesized from amino acids and citric acid cycle intermediates via glyconeogenesis pathway.

+ NAD(P)H + H⁺ →

+ NAD(P)⁺

Glycerol 1-phosphate is a starting material for de novo synthesis of archea-specific ether lipids, such as archaeol and caldarchaeol. It is first geranylgeranylated on its sn-3 position by a cytosolic enzyme, phosphoglycerol geranylgeranyltransferase, and another geranylgeranyl group is then added on the sn-2 position making unsaturated archaetidic acid, which is a key compound for synthesizing archeal lipids.[4]

+ GGPP → geranylgeranylglycerol phosphate + PPi

Enantiomer

Organisms other than archea uses the enantiomer, glycerol 3-phosphate. Most biochemical activities distinguish the two compounds.

Notes

This article uses stereospecific numbering where stereoconfiguration is not explicitly specified.
G. P. Moss (ed.). "Nomenclature of Phosphorus-Containing Compounds of Biochemical Importance". Archived from the original on 2016-12-08. Retrieved 2015-05-20.
Nishihara & Koga (1995). "sn-Glycerol-1-phosphate dehydrogenase in Methanobacterium thermoautotrophicum: key enzyme in biosynthesis of the enantiomeric glycerophosphate backbone of ether phospholipids of archaebacteria". J. Biochem. 117 (5): 933–935.
Koga & Morii (2007). "Biosynthesis of ether-type polar lipids in archaea and evolutionary considerations". Microbiol. Mol. Biol. Rev. 71 (1): 97–120. doi:10.1128/mmbr.00033-06. PMC 1847378. PMID 17347520.

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[1] This article uses stereospecific numbering where stereoconfiguration is not explicitly specified.

[phosphorus-2] G. P. Moss (ed.). "Nomenclature of Phosphorus-Containing Compounds of Biochemical Importance". Archived from the original on 2016-12-08. Retrieved 2015-05-20.

[3] Nishihara & Koga (1995). "sn-Glycerol-1-phosphate dehydrogenase in Methanobacterium thermoautotrophicum: key enzyme in biosynthesis of the enantiomeric glycerophosphate backbone of ether phospholipids of archaebacteria". J. Biochem. 117 (5): 933–935.

[4] Koga & Morii (2007). "Biosynthesis of ether-type polar lipids in archaea and evolutionary considerations". Microbiol. Mol. Biol. Rev. 71 (1): 97–120. doi:10.1128/mmbr.00033-06. PMC 1847378. PMID 17347520.