Glycerol 1-phosphate

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]

This article is about S-configulation. For R-configulation, see glycerol 3-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
3D model (JSmol)
MeSH Alpha-glycerophosphoric+acid
UNII
Properties
C3H9O6P
Molar mass 172.073 g·mol−1
Related compounds
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

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
  1. This article uses stereospecific numbering where stereoconfiguration is not explicitly specified.
  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. doi:10.1093/oxfordjournals.jbchem.a124822. PMID 8586635.
  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.
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