Glycerol 1-phosphate

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

sn-Glycerol 1-phosphate

Names
IUPAC name

sn-Glycerol 1-(dihydrogen phosphate)

Systematic 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

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

Tracking categories (test):

* SizeSet

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

## Contents

* 1 Biosynthesis and metabolism
* 2 Lipid divide
* 3 See also
* 4 Notes

## 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] (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[update], biologists still do not know how the lipid divide happened.[5]

It is known from genetic engineering that cells (specifically modified E. coli) that produce both types of lipids at the same time are viable.[6] 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.[7] 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.[8]

## See also

* List of unsolved problems in biology

## Notes

1. ↑ This article uses stereospecific numbering where stereoconfiguration is not explicitly specified.

1. ↑ 1.0 1.1 G. P. Moss, ed. "Nomenclature of Phosphorus-Containing Compounds of Biochemical Importance". http://www.chem.qmul.ac.uk/iupac/misc/phospho.html.
2. ↑ 2.0 2.1 Caforio, Antonella; Driessen, Arnold J.M. (2017). "Archaeal phospholipids: Structural properties and biosynthesis". 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. https://pure.rug.nl/ws/files/49238927/1_s2.0_S1388198116303432_main.pdf.
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. PMID 17347520.
5. ↑ Sohlenkamp, C (July 2021). "Crossing the lipid divide.". The Journal of Biological Chemistry 297 (1). doi:10.1016/j.jbc.2021.100859. PMID 34097872.
6. ↑ Yokoi, Takeru; Isobe, Keisuke; Yoshimura, Tohru; Hemmi, Hisashi (2012). "Archaeal Phospholipid Biosynthetic Pathway Reconstructed in Escherichia coli". Archaea 2012: 1–9. doi:10.1155/2012/438931. PMID 22645416.
7. ↑ Villanueva, Laura; Bastiaan von Meijenfeldt, F A; Westbye, Alexander B; Yadav, Subhash; Hopmans, Ellen C; Dutilh, Bas E; Sinninghe Damsté, Jaap S (1 January 2021). "Bridging the membrane lipid divide: bacteria of the FCB group superphylum have the potential to synthesize archaeal ether lipids". The ISME Journal 15 (1): 168–182. doi:10.1038/s41396-020-00772-2. PMID 32929208. Bibcode: 2021ISMEJ..15..168V.
8. ↑ Goode, Olivia; Łapińska, Urszula; Morimoto, Juliano; Glover, Georgina; Milner, David S.; Santoro, Alyson E.; Pagliara, Stefano; Richards, Thomas A. (20 May 2025). "Permeability selection of biologically relevant membranes matches the stereochemistry of life on Earth". PLOS Biology 23 (5). doi:10.1371/journal.pbio.3003155. PMID 40392769.

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