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Glycerol 1-phosphate

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This article is about S-configulation. For R-configulation, see glycerol 3-phosphate.
sn-Glycerol 1-phosphate
Names
Preferred IUPAC name (2S)-2,3-Dihydroxypropyl 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
glycero-1-phosphate
O-phosphonoglycerol
1-phosphoglycerol
L-glycerol 1-phosphate
D-glycerol 3-phosphate
D-α-glycerophosphoric acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH Alpha-glycerophosphoric+acid
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m0/s1Key: AWUCVROLDVIAJX-VKHMYHEASA-N
SMILES
  • C((COP(=O)(O)O)O)O
Properties
Chemical formula C3H7O6P
Molar mass 170.057 g·mol
Appearance colorless
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 , 100 kPa). Infobox references
Chemical compound

sn-Glycerol 1-phosphate is the conjugate base of a phosphoric ester of glycerol. It is a component of ether lipids, which are common for archaea.

Biosynthesis and metabolism

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

DHAP + NAD(P)H + H → G1P + NAD(P)

Glycerol 1-phosphate is a starting material for de novo synthesis of ether lipids, such as those derived from archaeol and caldarchaeol. It is first geranylgeranylated on its sn-3 position by a cytosolic enzyme, phosphoglycerol geranylgeranyltransferase. A second geranylgeranyl group is then added on the sn-2 position making unsaturated archaetidic acid.

Lipid divide

Organisms other than archaea, i.e. bacteria and eukaryotes, use the enantiomer, glycerol 3-phosphate for producing their cell membranes. The fact that archaea use the flipped chirality compared to these two groups is termed a lipid divide. As of 2021, biologists still do not know how the lipid divide happened.

See also

Notes

  1. This article uses stereospecific numbering where stereoconfiguration is not explicitly specified.
  1. ^ G. P. Moss (ed.). "Nomenclature of Phosphorus-Containing Compounds of Biochemical Importance". Archived from the original on 2016-12-08. Retrieved 2015-05-20.
  2. ^ Caforio, Antonella; Driessen, Arnold J.M. (2017). "Archaeal phospholipids: Structural properties and biosynthesis" (PDF). Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1862 (11): 1325–1339. doi:10.1016/j.bbalip.2016.12.006. PMID 28007654. S2CID 27154462.
  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.
  5. Sohlenkamp, C (July 2021). "Crossing the lipid divide". The Journal of Biological Chemistry. 297 (1): 100859. doi:10.1016/j.jbc.2021.100859. PMC 8220414. PMID 34097872.
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