{{About|''S''-configulation|''R''-configulation|glycerol 3-phosphate}} {{Chembox | Name = ''sn''-Glycerol 1-phosphate | ImageFile = Glycerol 1-phosphateDianion.svg | ImageSize = 180 | SystematicName = (2''S'')-2,3-Dihydroxypropyl dihydrogen phosphate |IUPACName=''sn''-Glycerol 1-(dihydrogen phosphate) | OtherNames = (''S'')-2,3-dihydroxypropyl dihydrogen phosphate<br />1,2,3-propanetriol, 1-(dihydrogen phosphate), (2''S'')-<br />{{Smaller|L}}-glycerol 1-phosphate<br />{{Smaller|D}}-glycerol 3-phosphate<br />{{Smaller|D}}-α-glycerophosphate<br />{{Smaller|D}}-α-phosphoglycerol<br/>glycero-1-phosphate<br/>O-phosphonoglycerol<br/>1-phosphoglycerol<ref name="phosphorus">{{cite web|editor=G. P. Moss|title=Nomenclature of Phosphorus-Containing Compounds of Biochemical Importance|url=http://www.chem.qmul.ac.uk/iupac/misc/phospho.html|access-date=2015-05-20|archive-url=https://web.archive.org/web/20161208003337/http://www.chem.qmul.ac.uk/iupac/misc/phospho.html|archive-date=2016-12-08}}</ref><br/>{{Smaller|L}}-glycerol 1-phosphate<br/>{{Smaller|D}}-glycerol 3-phosphate<br/>{{Smaller|D}}-α-glycerophosphoric acid<ref name="phosphorus" /> | Section1 = {{Chembox Identifiers | CASNo = 5746-57-6 | CASNo_Ref = {{cascite|correct|CAS}} | ChEBI = 16221 | ChemSpiderID = 388409 | KEGG = C00623 | PubChem = 439276 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 196623779E | StdInChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m0/s1 | StdInChIKey = AWUCVROLDVIAJX-VKHMYHEASA-N | SMILES = C([C@@H](COP(=O)(O)O)O)O | MeSHName = Alpha-glycerophosphoric+acid }} | Section2 = {{Chembox Properties | C=3|H=7|O=6|P=1 | Appearance = colorless | Density = | MeltingPt = | BoilingPt = }} | Section9 = {{Chembox Related | OtherFunction = Glycerol 2-phosphate<br />Glycerol 3-phosphate | OtherFunction_label = organophosphates }} }}
'''''sn''-Glycerol 1-phosphate'''{{efn|This article uses stereospecific numbering where stereoconfiguration is not explicitly specified.}} is the conjugate base of a phosphoric ester of glycerol. It is a component of ether lipids, which are common for archaea.<ref name=Caforio>{{cite journal |doi=10.1016/j.bbalip.2016.12.006|title=Archaeal phospholipids: Structural properties and biosynthesis |year=2017 |last1=Caforio |first1=Antonella |last2=Driessen |first2=Arnold J.M. |journal=Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids |volume=1862 |issue=11 |pages=1325–1339 |pmid=28007654 |s2cid=27154462 |url=https://pure.rug.nl/ws/files/49238927/1_s2.0_S1388198116303432_main.pdf }}</ref>
== Biosynthesis and metabolism == Glycerol 1-phosphate is synthesized by reducing dihydroxyacetone phosphate (DHAP), a glycolysis intermediate, with ''sn''-glycerol-1-phosphate dehydrogenase.<ref>{{cite journal|author=Nishihara & Koga|year=1995|title=''sn''-Glycerol-1-phosphate dehydrogenase in ''Methanobacterium thermoautotrophicum'': key enzyme in biosynthesis of the enantiomeric glycerophosphate backbone of ether phospholipids of archaebacteria|journal=J. Biochem.|volume=117|issue=5|pages=933–935|doi=10.1093/oxfordjournals.jbchem.a124822|pmid=8586635}}</ref> DHAP and thus glycerol 1-phosphate is also possible to be synthesized from amino acids and citric acid cycle intermediates via gluconeogenesis pathway. :x40px|DHAP + NAD(P)H + H<sup>+</sup> → x40px|G1P + NAD(P)<sup>+</sup>
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.<ref>{{cite journal|author=Koga & Morii|year=2007|title=Biosynthesis of ether-type polar lipids in archaea and evolutionary considerations|journal=Microbiol. Mol. Biol. Rev.|volume=71|issue=1|pages=97–120|url= |doi=10.1128/mmbr.00033-06|pmid=17347520|pmc=1847378}}</ref>
== 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'''.<ref name=Caforio/> (The other part of the lipid divide is that archaea use ether lipids while bacteria and eukarya use ester lipids, though this has turned out to be a lot less strict than the chirality divide.) {{As of|2021}}, biologists still do not know how the lipid divide happened.<ref>{{cite journal |last1=Sohlenkamp |first1=C |title=Crossing the lipid divide. |journal=The Journal of Biological Chemistry |date=July 2021 |volume=297 |issue=1 |article-number=100859 |doi=10.1016/j.jbc.2021.100859 |pmid=34097872 |pmc=8220414 |doi-access=free }}</ref>
It is known from genetic engineering that cells (specifically modified ''E. coli'') that produce both types of lipids at the same time are viable.<ref>{{cite journal |last1=Yokoi |first1=Takeru |last2=Isobe |first2=Keisuke |last3=Yoshimura |first3=Tohru |last4=Hemmi |first4=Hisashi |title=Archaeal Phospholipid Biosynthetic Pathway Reconstructed in Escherichia coli |journal=Archaea |date=2012 |volume=2012 |pages=1–9 |doi=10.1155/2012/438931|doi-access=free |pmid=22645416 |pmc=3357500 }}</ref> Genetic evidence for a natural mixed-membrane system have also been found, pending definitive proof by chemical analysis. This lends to the idea that the common ancestor of bacteria and archaea, especially the last universal common ancestor, may have had a mixed membrane.<ref>{{cite journal |last1=Villanueva |first1=Laura |last2=Bastiaan von Meijenfeldt |first2=F A |last3=Westbye |first3=Alexander B |last4=Yadav |first4=Subhash |last5=Hopmans |first5=Ellen C |last6=Dutilh |first6=Bas E |last7=Sinninghe Damsté |first7=Jaap S |title=Bridging the membrane lipid divide: bacteria of the FCB group superphylum have the potential to synthesize archaeal ether lipids |journal=The ISME Journal |date=1 January 2021 |volume=15 |issue=1 |pages=168–182 |doi=10.1038/s41396-020-00772-2 |doi-access=free|pmid=32929208 |bibcode=2021ISMEJ..15..168V |pmc=7852524 }}</ref> Assuming this is the case, this still leaves open the question of why most current life forms only use one of these chiralities. One hypothesis involves the permeability of mixed and non-mixed membranes to common building blocks of life.<ref>{{cite journal |last1=Goode |first1=Olivia |last2=Łapińska |first2=Urszula |last3=Morimoto |first3=Juliano |last4=Glover |first4=Georgina |last5=Milner |first5=David S. |last6=Santoro |first6=Alyson E. |last7=Pagliara |first7=Stefano |last8=Richards |first8=Thomas A. |title=Permeability selection of biologically relevant membranes matches the stereochemistry of life on Earth |journal=PLOS Biology |date=20 May 2025 |volume=23 |issue=5 |article-number=e3003155 |doi=10.1371/journal.pbio.3003155|doi-access=free |pmid=40392769 |pmc=12091744 }}</ref>
== See also == * List of unsolved problems in biology
== Notes == {{notelist}} {{reflist}}
Category:Organophosphates Category:Glycerol esters