2.02012-10-24 09:54:59 -06002015-09-16 17:34:54 -0600ECMDB23680M2MDB004070PG(14:0(3-OH)/19:iso)PG(14:0(3-OH)/19:iso) 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)/19:iso), in particular, consists of one 3-hydroxytetradecanoyl chain to the C-1 atom, and one 17-methylocatdecanoyl 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-2-17-methylocatdecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-3-hydroxytetradecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol1-3-hydroxytetradecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerolGPG(14:0/19:0)GPG(33:0)PG(14:0/19:0)PG(33:0)Phosphatidylglycerol(14:0/19:0)Phosphatidylglycerol(33:0)C39H77O11P752.9958752.520349818(2,3-dihydroxypropoxy)({3-[(3-hydroxytetradecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acid2,3-dihydroxypropoxy(3-[(3-hydroxytetradecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acidCCCCCCCCCCCC(O)CC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)CInChI=1S/C39H77O11P/c1-4-5-6-7-8-14-18-21-24-27-35(41)29-39(44)47-32-37(33-49-51(45,46)48-31-36(42)30-40)50-38(43)28-25-22-19-16-13-11-9-10-12-15-17-20-23-26-34(2)3/h34-37,40-42H,4-33H2,1-3H3,(H,45,46)PVFOCSARRACPHJ-UHFFFAOYSA-NSolidMembranelogp6.89logs-6.53solubility2.23e-04 g/llogp9.99pka_strongest_acidic1.89pka_strongest_basic-2.8iupac(2,3-dihydroxypropoxy)({3-[(3-hydroxytetradecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acidaverage_mass752.9958mono_mass752.520349818smilesCCCCCCCCCCCC(O)CC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)CformulaC39H77O11PinchiInChI=1S/C39H77O11P/c1-4-5-6-7-8-14-18-21-24-27-35(41)29-39(44)47-32-37(33-49-51(45,46)48-31-36(42)30-40)50-38(43)28-25-22-19-16-13-11-9-10-12-15-17-20-23-26-34(2)3/h34-37,40-42H,4-33H2,1-3H3,(H,45,46)inchikeyPVFOCSARRACPHJ-UHFFFAOYSA-Npolar_surface_area169.05refractivity201.37polarizability90.14rotatable_bond_count40acceptor_count7donor_count4physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(17:0cycw7c/17:0cycw7c/14:0/19:0cycv8c))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.PW001707MetabolicSpecdb::CMs1087049Specdb::NmrOneD260488Specdb::NmrOneD260489Specdb::NmrOneD260490Specdb::NmrOneD260491Specdb::NmrOneD260492Specdb::NmrOneD260493Specdb::NmrOneD260494Specdb::NmrOneD260495Specdb::NmrOneD260496Specdb::NmrOneD260497Specdb::NmrOneD260498Specdb::NmrOneD260499Specdb::NmrOneD260500Specdb::NmrOneD260501Specdb::NmrOneD260502Specdb::NmrOneD260503Specdb::NmrOneD260504Specdb::NmrOneD260505Specdb::NmrOneD260506Specdb::NmrOneD260507Specdb::MsMs24704Specdb::MsMs24705Specdb::MsMs24706Specdb::MsMs31262Specdb::MsMs31263Specdb::MsMs31264Kanehisa, 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):5185-9622753057Casadei MA, Mañas P, Niven G, Needs E, Mackey BM. (2002) "Role of membrane fluidity in pressure resistance of Escherichia coli NCTC 8164." Appl Environ Microbiol. 68(12):5965-72.12450817Yurtsever 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.xmlPG(14:0(3-OH)/19:iso) + PE(17:0cycw7c/17:0cycw7c) > Ethanolamine + CL(17:0cycw7c/17:0cycw7c/14:0/19:0cycv8c)PW_R0050762 PGP(14:0(3-OH)/19:iso) + Water >2 PG(14:0(3-OH)/19:iso) + PhosphatePW_R005733