''sn''-Glycerol 1-phosphate is the conjugate base of a

phosphoric ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fa ...

glycerol Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...

. It is a component of

ether lipid In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

s, which are common for

archaea Archaea ( ; singular archaeon ) is a domain of single-celled organisms. These microorganisms lack cell nuclei and are therefore prokaryotes. Archaea were initially classified as bacteria, receiving the name archaebacteria (in the Archaebac ...

Biosynthesis and metabolism

Glycerol 1-phosphate is synthesized by reducing

dihydroxyacetone phosphate Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is the anion with the formula HOCH2C(O)CH2OPO32-. This anion is involved in many metabolic pathways, including the Calvin cycle in plants and glycolysis.Nelson, D. L.; ...

(DHAP), a

glycolysis Glycolysis is the metabolic pathway that converts glucose () into pyruvate (). The free energy released in this process is used to form the high-energy molecules adenosine triphosphate (ATP) and reduced nicotinamide adenine dinucleotide (NADH ...

intermediate, with ''sn''-glycerol-1-phosphate dehydrogenase. DHAP and thus glycerol 1-phosphate is also possible to be synthesized from

amino acids Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha am ...

and

citric acid cycle The citric acid cycle (CAC)—also known as the Krebs cycle or the TCA cycle (tricarboxylic acid cycle)—is a series of chemical reactions to release stored energy through the oxidation of acetyl-CoA derived from carbohydrates, fats, and proteins ...

intermediates via

gluconeogenesis Gluconeogenesis (GNG) is a metabolic pathway that results in the generation of glucose from certain non-carbohydrate carbon substrates. It is a ubiquitous process, present in plants, animals, fungi, bacteria, and other microorganisms. In vertebrat ...

pathway. : Dihydroxyacetonphosphat Skelett

+ NAD(P)H + H⁺ → Glycerin-1-phosphat Skelett

+ NAD(P)⁺ Glycerol 1-phosphate is a starting material for ''de novo'' synthesis of ether lipids, such as those derived from

archaeol Archaeol is composed of two phytanyl chains linked to the sn-2 and sn-3 positions of glycerol. As its phosphate ester, it is a common component of the membranes of archaea. Structure and contrast with other lipids Archaeol is a diether. The 2 ...

and

caldarchaeol Caldarchaeol is a membrane-spanning lipid found in hyperthermophilic archaea. Membranes made up of caldarchaeol are more stable since the hydrophobic chains are linked together, allowing the microorganisms to withstand high temperatures. It is a ...

. It is first geranylgeranylated on its ''sn''-3 position by a cytosolic enzyme,

phosphoglycerol geranylgeranyltransferase In enzymology, a phosphoglycerol geranylgeranyltransferase () is an enzyme that catalyzes the chemical reaction :geranylgeranyl diphosphate + ''sn''-glyceryl 1-phosphate \rightleftharpoons diphosphate + ''sn''-3-''O''-(geranylgeranyl)glyceryl 1- ...

. A second geranylgeranyl group is then added on the ''sn''-2 position making unsaturated archaetidic acid.

Enantiomer

Organisms other than archaea, i.e.

bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among ...

and eucarya, use the

enantiomer In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...

glycerol 3-phosphate ''sn''-Glycerol 3-phosphate is the organic ion with the formula HOCH2CH(OH)CH2OPO32-. It is one of three stereoisomers of the ester of dibasic phosphoric acid (HOPO32-) and glycerol. It is a component of glycerophospholipids. Equally appropriat ...

for producing their cell membranes.

Notes

{{reflist Organophosphates Phosphate esters