Glycerol 1-phosphate
 | |
| Names | |
|---|---|
| IUPAC name
(S)-2,3-dihydroxypropyl dihydrogen phosphate | |
| Other names
1,2,3-propanetriol, 1-(dihydrogen phosphate), (2S)- L-glycerol 1-phosphate D-glycerol 3-phosphate D-α-glycerophosphate D-α-phosphoglycerol | |
| Identifiers | |
| 5746-57-6 | |
| 3D model (Jmol) | Interactive image |
| MeSH | Alpha-glycerophosphoric+acid |
| PubChem | 439276 |
| |
| Properties | |
| C3H9O6P | |
| Molar mass | 172.074 |
| 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]
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.
- 1 2 G. P. Moss (ed.). "Nomenclature of Phosphorus-Containing Compounds of Biochemical Importance". 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.