| Record Information |
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| Version | 2.0 |
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| Creation Date | 2012-07-30 14:55:00 -0600 |
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| Update Date | 2015-06-03 17:20:56 -0600 |
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| Secondary Accession Numbers | |
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| Identification |
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| Name: | Glycerophosphoserine |
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| Description | Glycerophosphoserine is a phosphodiester. Glycerophosphoserine is a source of phosphate and glycerol for bacteria. Escherichia coli cytosolic glycerophosphodiester phosphodiesterase, UgpQ has broad substrate specificity toward various glycerophosphodiesters, producing sn-glycerol-3-phosphate and the corresponding alcohols. UgpQ accumulates under conditions of phosphate starvation, suggesting that it allows the utilization of glycerophosphodiesters as a source of phosphate. E. coli K12 possesses two systems the salvage of glycerophosphoryl diesters, the Glp system and the Ugp system. In the Glp system, the glpQ gene encodes a periplasmic glycerophosphoryl diester phosphodiesterase (periplasmic GDP) which hydrolyzes deacylated phospholipids to an alcohol and sn-glycerol-3-phosphate. The latter is then transported into the cell by the GlpT transporter. Periplasmic GDP is specific for the glycerophospho- moiety of the substrate, while the alcohol can be any one of several alcohols. This provides the cell with the capability of channeling a wide variety of glycerophosphodiesters into the glpQT-encoded dissimilatory system. In the Ugp system the diesters are hydrolyzed during transport at the cytoplasmic side of the inner membrane to sn-glycerol-3-phosphate and an alcohol by a cytoplasmic GDP, an enzyme encoded by the ugpQ gene. The Ugp system is induced when the cells are starved for inorganic phospate, which is generates phosphate by the system. In E. coli sn-glycerol-3-phosphate can be further metabolized to dihydroxyacetone phosphate by either of two membrane-bound enzymes, depending on the growth conditions. The presumed role of this process is the salvage of glycerol and glycerol phosphates generated by the breakdown of phospholipids and triacylglycerol. |
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| Structure | |
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| Synonyms: | - (2S)-2-azaniumyl-3-{[(2,3-dihydroxypropoxy)phosphinato]oxy}propanoate
- (2S)-2-azaniumyl-3-{[(2,3-dihydroxypropoxy)phosphinato]oxy}propanoic acid
- 1-Glycerophosphoserine(1)
- Glycerophosphoserine
- Glycerophosphoserine(1)
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| Chemical Formula: | C6H14NO8P |
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| Weight: | Average: 259.151
Monoisotopic: 259.045702941 |
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| InChI Key: | ZWZWYGMENQVNFU-AKGZTFGVSA-N |
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| InChI: | InChI=1S/C6H14NO8P/c7-5(6(10)11)3-15-16(12,13)14-2-4(9)1-8/h4-5,8-9H,1-3,7H2,(H,10,11)(H,12,13)/t4?,5-/m0/s1 |
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| CAS number: | Not Available |
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| IUPAC Name: | (2S)-2-amino-3-{[(2,3-dihydroxypropoxy)(hydroxy)phosphoryl]oxy}propanoic acid |
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| Traditional IUPAC Name: | 1-glycerophosphoserine |
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| SMILES: | [H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])OP(=O)(O[H])OC([H])([H])C([H])(O[H])C([H])([H])O[H] |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as glycerophosphoserines. These are lipids containing a glycerol moiety carrying a phosphoserine at the 3-position. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Glycerophospholipids |
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| Sub Class | Glycerophosphoserines |
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| Direct Parent | Glycerophosphoserines |
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| Alternative Parents | |
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| Substituents | - Glycerophosphoserine
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- Phosphoethanolamine
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Amino acid
- Secondary alcohol
- Amino acid or derivatives
- 1,2-diol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Alcohol
- Primary aliphatic amine
- Organopnictogen compound
- Primary alcohol
- Carbonyl group
- Primary amine
- Amine
- Organic oxygen compound
- Organic nitrogen compound
- Organic oxide
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State: | Not Available |
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| Charge: | -1 |
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| Melting point: | Not Available |
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| Experimental Properties: | |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations: | Cytoplasm |
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| Reactions: | |
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| SMPDB Pathways: | Not Available |
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| KEGG Pathways: | Not Available |
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| EcoCyc Pathways: | Not Available |
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| Concentrations |
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| Not Available |
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| Spectra |
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| Spectra: | |
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| References |
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| References: | Not Available |
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| Synthesis Reference: | Not Available |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| Links |
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| External Links: | |
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