2.02012-10-24 09:54:59 -06002015-12-09 12:06:51 -0700ECMDB23678M2MDB004068PG(14:0(3-OH)/18:1(9Z))PG(14:0(3-OH)/18:1(9Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(14:0(3-OH)/18:1(9Z)), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.1-3-hydroxytetradecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)1-3-hydroxytetradecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoglycerol1-3-hydroxytetradecanoyl-2-oleoyl-sn-glycero-3-phosphoglycerolGPG(14:0/18:1)GPG(32:1)PG(14:0/18:1)PG(32:1)Phosphatidylglycerol(14:0/18:1)Phosphatidylglycerol(32:1)C38H73O11P736.965736.489050169[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy((2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CC(O)CCCCCCCCCCCInChI=1S/C38H73O11P/c1-3-5-7-9-11-13-14-15-16-17-18-20-22-24-26-28-37(42)46-32-36(33-48-50(44,45)47-31-35(41)30-39)49-38(43)29-34(40)27-25-23-21-19-12-10-8-6-4-2/h15-16,34-36,39-41H,3-14,17-33H2,1-2H3,(H,44,45)/b16-15-/t34?,35-,36+/m0/s1YZWXTZVNFIEAJY-TXMSSCOLSA-NSolidMembranelogp6.75logs-6.45solubility2.63e-04 g/llogp9.34pka_strongest_acidic1.89pka_strongest_basic-2.8iupac[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(3-hydroxytetradecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acidaverage_mass736.965mono_mass736.489050169smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CC(O)CCCCCCCCCCCformulaC38H73O11PinchiInChI=1S/C38H73O11P/c1-3-5-7-9-11-13-14-15-16-17-18-20-22-24-26-28-37(42)46-32-36(33-48-50(44,45)47-31-35(41)30-39)49-38(43)29-34(40)27-25-23-21-19-12-10-8-6-4-2/h15-16,34-36,39-41H,3-14,17-33H2,1-2H3,(H,44,45)/b16-15-/t34?,35-,36+/m0/s1inchikeyYZWXTZVNFIEAJY-TXMSSCOLSA-Npolar_surface_area169.05refractivity197.94polarizability87.27rotatable_bond_count39acceptor_count7donor_count4physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(17:0cycw7c/17:0cycw7c/14:0/18:1(9Z)))Phospholipids are membrane components in E. coli.
The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions.
The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed to a sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH driven glycerol-3-phosphate dehydrogenase.
Sn-glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate(1-oleyl-2-lyso-phosphatidate , 1-palmitoylglycerol 3-phosphate , 1-stearoyl-sn-glycerol 3-phosphate). This can be achieve by a sn-glycerol-3-phosphate 1-0-acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate through a 1-acylglycerol-3-phosphate O-acyltransferase.
This compound is then converted into a CPD-diacylglycerol through a CTP (phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either to a L-1-phosphatidylserine or a L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase, o the other hand L-1-phosphatidylglycerol-phosphate gets transformed into a L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combines produce a cardiolipin and a ethanolamine.
The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin.PW001706Metabolicphospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/14:0/18:1(9Z)))Phospholipids are membrane components in E. coli.
The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions.
The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed to a sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH driven glycerol-3-phosphate dehydrogenase.
Sn-glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate(1-oleyl-2-lyso-phosphatidate , 1-palmitoylglycerol 3-phosphate , 1-stearoyl-sn-glycerol 3-phosphate). This can be achieve by a sn-glycerol-3-phosphate 1-0-acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate through a 1-acylglycerol-3-phosphate O-acyltransferase.
This compound is then converted into a CPD-diacylglycerol through a CTP (phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either to a L-1-phosphatidylserine or a L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase, o the other hand L-1-phosphatidylglycerol-phosphate gets transformed into a L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combines produce a cardiolipin and a ethanolamine.
The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin.PW001514MetabolicSpecdb::CMs1083717Specdb::NmrOneD259588Specdb::NmrOneD259589Specdb::NmrOneD259590Specdb::NmrOneD259591Specdb::NmrOneD259592Specdb::NmrOneD259593Specdb::NmrOneD259594Specdb::NmrOneD259595Specdb::NmrOneD259596Specdb::NmrOneD259597Specdb::NmrOneD259598Specdb::NmrOneD259599Specdb::NmrOneD259600Specdb::NmrOneD259601Specdb::NmrOneD259602Specdb::NmrOneD259603Specdb::NmrOneD259604Specdb::NmrOneD259605Specdb::NmrOneD259606Specdb::NmrOneD259607Specdb::MsMs1249315Specdb::MsMs1249316Specdb::MsMs1249317Specdb::MsMs1364617Specdb::MsMs1364618Specdb::MsMs1364619Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-9622753057Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.ALysophospholipase L2P07000PLDB_ECOLIpldBhttp://ecmdb.ca/proteins/P07000.xmlPhosphatidylglycerophosphatase BP0A924PGPB_ECOLIpgpBhttp://ecmdb.ca/proteins/P0A924.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.xmlProtein crcAP37001CRCA_ECOLIcrcAhttp://ecmdb.ca/proteins/P37001.xmlCardiolipin synthaseP0A6H8CLS_ECOLIclshttp://ecmdb.ca/proteins/P0A6H8.xmlPutative cardiolipin synthase ybhOP0AA84YBHO_ECOLIybhOhttp://ecmdb.ca/proteins/P0AA84.xmlCardiolipin synthase CP75919CLSC_ECOLIclsChttp://ecmdb.ca/proteins/P75919.xmlProbable phospholipid ABC transporter-binding protein mlaBP64602MLAB_ECOLImlaBhttp://ecmdb.ca/proteins/P64602.xmlLipid A export ATP-binding/permease protein msbAP60752MSBA_ECOLImsbAhttp://ecmdb.ca/proteins/P60752.xmlProbable phospholipid ABC transporter-binding protein mlaDP64604MLAD_ECOLImlaDhttp://ecmdb.ca/proteins/P64604.xmlProbable phospholipid ABC transporter permease protein mlaEP64606MLAE_ECOLImlaEhttp://ecmdb.ca/proteins/P64606.xmlPE(15:0/18:1(9Z)) + PG(14:0(3-OH)/18:1(9Z)) + PE(18:1(9Z)/15:0cyclo) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/14:0/18:1(9Z))PW_R004844PG(14:0(3-OH)/18:1(9Z)) + PE(17:0cycw7c/17:0cycw7c) > Ethanolamine + CL(17:0cycw7c/17:0cycw7c/14:0/18:1(9Z))PW_R0050752 PGP(14:0(3-OH)/18:1(9Z)) + Water >2 PG(14:0(3-OH)/18:1(9Z)) + PhosphatePW_R005732