2.0 2012-07-30 14:55:00 -0600 2015-06-03 17:20:55 -0600 ECMDB21223 M2MDB001631 Glycerophosphoglycerol Glycerophosphoglycerol is a substrate for glycerol and phosphate salvage in E. coli. 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. Bis(2,3-dihydroxypropyl) hydrogen phosphate Bis(2,3-dihydroxypropyl) hydrogen phosphoric acid Glycerophosphoglycerol C6H14O8P 245.1443 245.042628936 3-[(2,3-dihydroxypropyl phosphonato)oxy]propane-1,2-diol glycerophosphoglycerol(1-) OCC(O)COP([O-])(=O)OCC(O)CO InChI=1S/C6H15O8P/c7-1-5(9)3-13-15(11,12)14-4-6(10)2-8/h5-10H,1-4H2,(H,11,12)/p-1 LLCSXHMJULHSJN-UHFFFAOYSA-M Cytosol Extra-organism Periplasm logp -2.21 ALOGPS logs -0.78 ALOGPS solubility 4.32e+01 g/l ALOGPS logp -2.9 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic -3 ChemAxon iupac 3-[(2,3-dihydroxypropyl phosphonato)oxy]propane-1,2-diol ChemAxon average_mass 245.1443 ChemAxon mono_mass 245.042628936 ChemAxon smiles OCC(O)COP([O-])(=O)OCC(O)CO ChemAxon formula C6H14O8P ChemAxon inchi InChI=1S/C6H15O8P/c7-1-5(9)3-13-15(11,12)14-4-6(10)2-8/h5-10H,1-4H2,(H,11,12)/p-1 ChemAxon inchikey LLCSXHMJULHSJN-UHFFFAOYSA-M ChemAxon polar_surface_area 139.51 ChemAxon refractivity 47 ChemAxon polarizability 20.7 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon glycerol metabolism IV (glycerophosphoglycerol) 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 glycerophosphoglycerol 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. PW000917 Metabolic Specdb::MsMs 24800 Specdb::MsMs 24801 Specdb::MsMs 24802 Specdb::MsMs 31358 Specdb::MsMs 31359 Specdb::MsMs 31360 25202983 26332446 C03274 5457 GLYCEROPHOSPHOGLYCEROL Lysophospholipase L2 P07000 PLDB_ECOLI pldB http://ecmdb.ca/proteins/P07000.xml Glycerophosphoryl diester phosphodiesterase P09394 GLPQ_ECOLI glpQ http://ecmdb.ca/proteins/P09394.xml Acyl-CoA thioesterase I P0ADA1 TESA_ECOLI tesA http://ecmdb.ca/proteins/P0ADA1.xml sn-glycerol-3-phosphate import ATP-binding protein UgpC P10907 UGPC_ECOLI ugpC http://ecmdb.ca/proteins/P10907.xml Glycerophosphoryl diester phosphodiesterase_ P10908 UGPQ_ECOLI ugpQ http://ecmdb.ca/proteins/P10908.xml sn-glycerol-3-phosphate transport system permease protein ugpA P10905 UGPA_ECOLI ugpA http://ecmdb.ca/proteins/P10905.xml sn-glycerol-3-phosphate transport system permease protein ugpE P10906 UGPE_ECOLI ugpE http://ecmdb.ca/proteins/P10906.xml sn-glycerol-3-phosphate-binding periplasmic protein ugpB P0AG80 UGPB_ECOLI ugpB http://ecmdb.ca/proteins/P0AG80.xml sn-glycerol-3-phosphate import ATP-binding protein UgpC P10907 UGPC_ECOLI ugpC http://ecmdb.ca/proteins/P10907.xml sn-glycerol-3-phosphate transport system permease protein ugpA P10905 UGPA_ECOLI ugpA http://ecmdb.ca/proteins/P10905.xml sn-glycerol-3-phosphate transport system permease protein ugpE P10906 UGPE_ECOLI ugpE http://ecmdb.ca/proteins/P10906.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml sn-glycerol-3-phosphate-binding periplasmic protein ugpB P0AG80 UGPB_ECOLI ugpB http://ecmdb.ca/proteins/P0AG80.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + Glycerophosphoglycerol > ADP + Glycerophosphoglycerol + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Glycerophosphoglycerol > ADP + Glycerophosphoglycerol + Hydrogen ion + Phosphate 1-Acyl-sn-glycero-3-phosphoglycerol (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerophosphoglycerol + Hydrogen ion 1-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + Water > Glycerophosphoglycerol + Hydrogen ion + tetradecanoate (n-C14:0) 1-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Tetradecenoate (N-C14:1) 1-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Palmitic acid 1-Acyl-sn-glycero-3-phosphoglycerol (N-C16:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Hexadecenoate (n-C16:1) 1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecanoate (N-C18:0) 1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecenoate (N-C18:1) Glycerophosphoglycerol + Water > Glycerol + Glycerol 3-phosphate + Hydrogen ion 2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerophosphoglycerol + Hydrogen ion 2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + PG(12:0/12:0) > Acyl phosphatidylglycerol (N-C12:0) + Glycerophosphoglycerol 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + Water > Glycerophosphoglycerol + Hydrogen ion + tetradecanoate (n-C14:0) 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + PG(14:0/14:0) > Acyl phosphatidylglycerol (N-C14:0) + Glycerophosphoglycerol 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Tetradecenoate (N-C14:1) 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + PG(14:1(7Z)/14:1(7Z)) > Acyl phosphatidylglycerol (N-C14:1) + Glycerophosphoglycerol 2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Palmitic acid 2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + PG(16:0/16:0) > Acyl phosphatidylglycerol (N-C16:0) + Glycerophosphoglycerol 2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Hexadecenoate (n-C16:1) 2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:1) + PG(16:1(9Z)/16:1(9Z)) > Acyl phosphatidylglycerol (N-C16:1) + Glycerophosphoglycerol 2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecanoate (N-C18:0) 2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + PG(18:0/18:0) > Acyl phosphatidylglycerol (N-C18:0) + Glycerophosphoglycerol 2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecenoate (N-C18:1) 2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + PG(18:1(11Z)/18:1(11Z)) > Acyl phosphatidylglycerol (N-C18:1) + Glycerophosphoglycerol Glycerophosphoglycerol + Water > Benzyl alcohol + Hydrogen ion + Glycerol 3-phosphate PW_R003446