Glycerol 1-phosphate

Last updated
sn-Glycerol 1-phosphate
Glycerol 1-phosphateDianion.svg
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
3D model (JSmol)
MeSH Alpha-glycerophosphoric+acid
PubChem CID
UNII
  • C([C@@H](COP(=O)(O)O)O)O
Properties
C3H9O6P
Molar mass 172.073 g·mol−1
Appearancecolorless
Related compounds
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).

sn-Glycerol 1-phosphate [2] is the conjugate base of a phosphoric ester of glycerol. It is a component of ether lipids, which are common for archaea. [3]

Contents

Biosynthesis and metabolism

Glycerol 1-phosphate is synthesized by reducing dihydroxyacetone phosphate (DHAP), a glycolysis intermediate, with sn-glycerol-1-phosphate dehydrogenase. [4] DHAP and thus glycerol 1-phosphate is also possible to be synthesized from amino acids and citric acid cycle intermediates via gluconeogenesis pathway.

Dihydroxyacetonphosphat Skelett.svg + NAD(P)H + H+ Glycerin-1-phosphat Skelett.svg + 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. [5]

Enantiomer

Organisms other than archaea, i.e. bacteria and eucarya, use the enantiomer, glycerol 3-phosphate for producing their cell membranes.

Notes

  1. 1 2 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. This article uses stereospecific numbering where stereoconfiguration is not explicitly specified.
  3. 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.
  4. 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.
  5. 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.

Related Research Articles

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Nicotinamide adenine dinucleotide phosphate Chemical compound

Nicotinamide adenine dinucleotide phosphate, abbreviated NADP+ or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic reactions, such as the Calvin cycle and lipid and nucleic acid syntheses, which require NADPH as a reducing agent ('hydrogen source'). It is used by all forms of cellular life.

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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. It is the phosphate ester of dihydroxyacetone.

<span class="mw-page-title-main">Glycerophospholipid</span>

Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes. Two major classes are known: those for bacteria and eucaryote and a separate family for archaea.

Plasmalogen Subclass of Glycerophospholipids

Glycerophospholipids of biochemical relevance are divided into three subclasses based on the substitution present at the sn-1 position of the glycerol backbone: acyl, alkyl and alkenyl. Of these, the alkyl and alkenyl moiety in each case form an ether bond, which makes for two types of ether phospholipids, plasmanyl, and plasmenyl. Plasmalogens are plasmenyls with an ester linked lipid at the sn-2 position of the glycerol backbone, chemically designated 1-0(1Z-alkenyl)-2-acyl-glycerophospholipids. The lipid attached to the vinyl ether at sn-1 can be C16:0, C18:0, or C18:1, and the lipid attached to the acyl group at sn-2 can be C22:6 ω-3 or C20:4 ω-6, . Plasmalogens are classified according to their head group, mainly as PC plasmalogens (plasmenylcholines) and PE plasmalogens (plasmenylethalomines) Plasmalogens should not be confused with plasmanyls.

Ether lipid

In an organic chemistry general sense, an ether lipid implies an ether bridge between an alkyl group and an unspecified alkyl or aryl group, not necessarily glycerol. If glycerol is involved, the compound is called a glyceryl ether, which may take the form of an alkylglycerol, an alkyl acyl glycerol, or in combination with a phosphatide group, a phospholipid.

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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. From a historical reason, it is also known as L-glycerol 3-phosphate, D-glycerol 1-phosphate, L-α-glycerophosphoric acid.

Glycerol phosphate shuttle

The glycerol-3-phosphate shuttle is a mechanism that regenerates NAD+ from NADH, a by-product of glycolysis. The shuttle consists of the sequential activity of two proteins: GPD1 which transfers an electron pair from NADH to dihydroxyacetone phosphate (DHAP), forming glycerol-3-phosphate (G3P) and regenerating NAD+ needed to generate energy via glycolysis. The mitochondrial inner membrane protein GPD2 catalyzes the oxidation of G3P, regenerating DHAP in the cytosol and forming FADH2 in the mitochondrial matrix. In mammals, its activity in transporting reducing equivalents across the mitochondrial membrane is considered secondary to the malate-aspartate shuttle.

Glycerol-3-phosphate dehydrogenase Class of enzymes

Glycerol-3-phosphate dehydrogenase (GPDH) is an enzyme that catalyzes the reversible redox conversion of dihydroxyacetone phosphate to sn-glycerol 3-phosphate.

Phosphatidylglycerol

Phosphatidylglycerol is a glycerophospholipid found in pulmonary surfactant and in the plasma membrane where it directly activates lipid-gated ion channels.

In enzymology, a sn-glycerol-1-phosphate dehydrogenase (EC 1.1.1.261) is an enzyme that catalyzes the chemical reaction

Glycerol-3-phosphate dehydrogenase (NAD<sup>+</sup>)

In enzymology, a glycerol-3-phosphate dehydrogenase (NAD+) (EC 1.1.1.8) is an enzyme that catalyzes the chemical reaction

In enzymology, a glycerol-3-phosphate dehydrogenase [NAD(P)+] (EC 1.1.1.94) is an enzyme that catalyzes the chemical reaction

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.

1-Lysophosphatidylcholine

2-acyl-sn-glycero-3-phosphocholines are a class of phospholipids that are intermediates in the metabolism of lipids. Because they result from the hydrolysis of an acyl group from the sn-1 position of phosphatidylcholine, they are also called 1-lysophosphatidylcholine. The synthesis of phosphatidylcholines with specific fatty acids occurs through the synthesis of 1-lysoPC. The formation of various other lipids generates 1-lysoPC as a by-product.

Glycerol-3-phosphate dehydrogenase (quinone)

Glycerol-3-phosphate dehydrogenase (EC 1.1.5.3 is an enzyme with systematic name sn-glycerol 3-phosphate:quinone oxidoreductase. This enzyme catalyses the following chemical reaction

CDP-archaeol synthase is an enzyme with systematic name CTP:2,3-bis-O-(geranylgeranyl)-sn-glycero-1-phosphate cytidylyltransferase. This enzyme catalyses the following chemical reaction