2.0 2012-07-30 14:55:00 -0600 2015-06-03 17:20:56 -0600 ECMDB21224 M2MDB001632 Glycerophosphoserine 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. (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) C6H14NO8P 259.151 259.045702941 (2S)-2-amino-3-{[(2,3-dihydroxypropoxy)(hydroxy)phosphoryl]oxy}propanoic acid 1-glycerophosphoserine [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] 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 ZWZWYGMENQVNFU-AKGZTFGVSA-N Cytosol Extra-organism Periplasm logp -2.80 ALOGPS logs -1.12 ALOGPS solubility 1.96e+01 g/l ALOGPS logp -4.3 ChemAxon pka_strongest_acidic 1.51 ChemAxon pka_strongest_basic 9.38 ChemAxon iupac (2S)-2-amino-3-{[(2,3-dihydroxypropoxy)(hydroxy)phosphoryl]oxy}propanoic acid ChemAxon average_mass 259.151 ChemAxon mono_mass 259.045702941 ChemAxon 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] ChemAxon formula C6H14NO8P ChemAxon 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 ChemAxon inchikey ZWZWYGMENQVNFU-AKGZTFGVSA-N ChemAxon polar_surface_area 159.54 ChemAxon refractivity 49.65 ChemAxon polarizability 21.47 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1084144 Specdb::NmrOneD 329802 Specdb::NmrOneD 329803 Specdb::NmrOneD 329804 Specdb::NmrOneD 329805 Specdb::NmrOneD 329806 Specdb::NmrOneD 329807 Specdb::NmrOneD 329808 Specdb::NmrOneD 329809 Specdb::NmrOneD 329810 Specdb::NmrOneD 329811 Specdb::NmrOneD 329812 Specdb::NmrOneD 329813 Specdb::NmrOneD 329814 Specdb::NmrOneD 329815 Specdb::NmrOneD 329816 Specdb::NmrOneD 329817 Specdb::NmrOneD 329818 Specdb::NmrOneD 329819 Specdb::NmrOneD 329820 Specdb::NmrOneD 329821 Specdb::MsMs 24950 Specdb::MsMs 24951 Specdb::MsMs 24952 Specdb::MsMs 31508 Specdb::MsMs 31509 Specdb::MsMs 31510 3081457 2339060 61931 CPD0-2030 Glycerophosphoryl diester phosphodiesterase P09394 GLPQ_ECOLI glpQ http://ecmdb.ca/proteins/P09394.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 + Glycerophosphoserine > ADP + Glycerophosphoserine + Hydrogen ion + Phosphate Adenosine triphosphate + Water + Glycerophosphoserine > ADP + Glycerophosphoserine + Hydrogen ion + Phosphate Glycerophosphoserine + Water > Glycerol 3-phosphate + Hydrogen ion + L-Serine