Glycerol 1-phosphate
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| Names | |
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| 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 | |
3D model (JSmol)
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| MeSH | Alpha-glycerophosphoric+acid |
PubChemCID
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| UNII | |
CompTox Dashboard(EPA)
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| Properties | |
| C3H7O6P | |
| Molar mass | 170.057g·mol−1 |
| Appearance | colorless |
| Related compounds | |
Relatedorganophosphates
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Glycerol 2-phosphate Glycerol 3-phosphate |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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sn-Glycerol 1-phosphate[a]is the conjugate base of aphosphoric esterofglycerol.It is a component ofether lipids,which are common forarchaea.[2]
Biosynthesis and metabolism
[edit]Glycerol 1-phosphate is synthesized by reducingdihydroxyacetone phosphate(DHAP), aglycolysisintermediate, withsn-glycerol-1-phosphate dehydrogenase.[3]DHAP and thus glycerol 1-phosphate is also possible to be synthesized fromamino acidsandcitric acid cycleintermediates viagluconeogenesispathway.
+ NAD(P)H + H+→
+ NAD(P)+
Glycerol 1-phosphate is a starting material forde novosynthesis of ether lipids, such as those derived fromarchaeolandcaldarchaeol.It is first geranylgeranylated on itssn-3 position by a cytosolic enzyme,phosphoglycerol geranylgeranyltransferase.A second geranylgeranyl group is then added on thesn-2 position making unsaturated archaetidic acid.[4]
Lipid divide
[edit]Organisms other than archaea, i.e.bacteriaandeukaryotes,use theenantiomer,glycerol 3-phosphatefor producing their cell membranes. The fact that archaea use the flipped chirality compared to these two groups is termed alipid divide.[2]As of 2021, biologists still do not know how the lipid divide happened.[5]
See also
[edit]Notes
[edit]- ^This article usesstereospecific numberingwhere stereoconfiguration is not explicitly specified.
- ^abG. P. Moss (ed.)."Nomenclature of Phosphorus-Containing Compounds of Biochemical Importance".Archived fromthe originalon 2016-12-08.Retrieved2015-05-20.
- ^abCaforio, 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.PMID28007654.S2CID27154462.
- ^Nishihara & Koga (1995). "sn-Glycerol-1-phosphate dehydrogenase inMethanobacterium 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.PMID8586635.
- ^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.PMC1847378.PMID17347520.
- ^Sohlenkamp, C (July 2021)."Crossing the lipid divide".The Journal of Biological Chemistry.297(1): 100859.doi:10.1016/j.jbc.2021.100859.PMC8220414.PMID34097872.