Glycerol 1-phosphate

This article is about S-configulation. For R-configulation, see glycerol 3-phosphate.

sn-Glycerol 1-phosphate^[a] is the conjugate base of a phosphoric ester of glycerol. It is a component of ether lipids, which are common for archaea.^[2]

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[1] L-glycerol 1-phosphate D-glycerol 3-phosphate D-α-glycerophosphoric acid[1]
Identifiers
CAS Number	5746-57-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16221
ChemSpider	388409
KEGG	C00623
MeSH	Alpha-glycerophosphoric+acid
PubChem CID	439276
UNII	196623779E Y
CompTox Dashboard (EPA)	DTXSID501315267
InChI InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m0/s1 Key: AWUCVROLDVIAJX-VKHMYHEASA-N
SMILES C([C@@H](COP(=O)(O)O)O)O
Properties
Chemical formula	C3H7O6P
Molar mass	170.057 g·mol−1
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 [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 gluconeogenesis pathway.

+ NAD(P)H + H⁺ → + 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.^[4]

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.^[2] As of 2021^[update], biologists still do not know how the lipid divide happened.^[5]

See also

• List of unsolved problems in biology

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.