2.02015-09-08 17:50:25 -06002015-09-14 16:46:13 -0600ECMDB24250M2MDB006367 glycerophosphoserineGlycerophosphoserine 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.C6H13NO8P258.143258.0384269612-azaniumyl-3-[(2,3-dihydroxypropyl phosphonato)oxy]propanoate2-ammonio-3-[(2,3-dihydroxypropyl phosphonato)oxy]propanoate[NH3+]C(COP([O-])(=O)OCC(O)CO)C([O-])=OInChI=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)/p-1ZWZWYGMENQVNFU-UHFFFAOYSA-Mlogp-1.56logs-0.90solubility4.11e+01 g/llogp-4.3pka_strongest_acidic1.51pka_strongest_basic9.38iupac2-azaniumyl-3-[(2,3-dihydroxypropyl phosphonato)oxy]propanoateaverage_mass258.143mono_mass258.038426961smiles[NH3+]C(COP([O-])(=O)OCC(O)CO)C([O-])=OformulaC6H13NO8PinchiInChI=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)/p-1inchikeyZWZWYGMENQVNFU-UHFFFAOYSA-Mpolar_surface_area166.82refractivity70.66polarizability21.24rotatable_bond_count8acceptor_count6donor_count3physiological_charge-1formal_charge-1glycerol metabolism V (glycerophosphoserine)Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through glycerophosphoserine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.PW000918MetabolicSpecdb::NmrOneD344748Specdb::NmrOneD344749Specdb::NmrOneD344750Specdb::NmrOneD344751Specdb::NmrOneD344752Specdb::NmrOneD344753Specdb::NmrOneD344754Specdb::NmrOneD344755Specdb::NmrOneD344756Specdb::NmrOneD344757Specdb::NmrOneD344758Specdb::NmrOneD344759Specdb::NmrOneD344760Specdb::NmrOneD344761Specdb::NmrOneD344762Specdb::NmrOneD344763Specdb::NmrOneD344764Specdb::NmrOneD344765Specdb::NmrOneD344766Specdb::NmrOneD344767Specdb::MsMs29147Specdb::MsMs29148Specdb::MsMs29149Specdb::MsMs35705Specdb::MsMs35706Specdb::MsMs35707Glycerophosphoryl diester phosphodiesteraseP09394GLPQ_ECOLIglpQhttp://ecmdb.ca/proteins/P09394.xmlGlycerophosphoryl diester phosphodiesterase_P10908UGPQ_ECOLIugpQhttp://ecmdb.ca/proteins/P10908.xml glycerophosphoserine + Water > Hydrogen ion + Benzyl alcohol + Glycerol 3-phosphatePW_R003447