2.02012-10-24 09:54:58 -06002015-12-09 12:06:42 -0700ECMDB23672M2MDB004062PG(14:0(3-OH)/14:0(3-OH))PG(14:0(3-OH)/14:0(3-OH)) 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)/14:0(3-OH)), in particular, consists of two 3-hydroxytetradecanoyl chains at positions C-1 and C-2. 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.1,2-di3-hydroxytetradecanoyl-rac-glycero-3-phospho-(1'-glycerol)1,2-di3-hydroxytetradecanoyl-rac-glycero-3-phosphoglycerol1,2-di3-hydroxytetradecanoyl-rac-glycero-3-phosphoglycerolGPG(14:0/14:0)GPG(28:0)PG(14:0/14:0)PG(28:0)Phosphatidylglycerol(14:0/14:0)Phosphatidylglycerol(28:0)C34H67O12P698.872698.437014595[(2R)-2,3-bis[(3-hydroxytetradecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid(2R)-2,3-bis[(3-hydroxytetradecanoyl)oxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCCCCInChI=1S/C34H67O12P/c1-3-5-7-9-11-13-15-17-19-21-29(36)23-33(39)43-27-32(28-45-47(41,42)44-26-31(38)25-35)46-34(40)24-30(37)22-20-18-16-14-12-10-8-6-4-2/h29-32,35-38H,3-28H2,1-2H3,(H,41,42)/t29?,30?,31-,32+/m0/s1DFZLNTBHFLVYEQ-VJUQQTGUSA-NSolidMembranelogp4.88logs-5.63solubility1.65e-03 g/llogp6.7pka_strongest_acidic1.89pka_strongest_basic-2.8iupac[(2R)-2,3-bis[(3-hydroxytetradecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acidaverage_mass698.872mono_mass698.437014595smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCCCCCformulaC34H67O12PinchiInChI=1S/C34H67O12P/c1-3-5-7-9-11-13-15-17-19-21-29(36)23-33(39)43-27-32(28-45-47(41,42)44-26-31(38)25-35)46-34(40)24-30(37)22-20-18-16-14-12-10-8-6-4-2/h29-32,35-38H,3-28H2,1-2H3,(H,41,42)/t29?,30?,31-,32+/m0/s1inchikeyDFZLNTBHFLVYEQ-VJUQQTGUSA-Npolar_surface_area189.28refractivity179.94polarizability80.5rotatable_bond_count36acceptor_count8donor_count5physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(17:0cycw7c/10:0(3-OH)/14:0/14:0))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.
PW001966MetabolicSpecdb::CMs1085006Specdb::MsMs1230388Specdb::MsMs1230389Specdb::MsMs1230390Specdb::MsMs1345927Specdb::MsMs1345928Specdb::MsMs1345929Kanehisa, 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.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.xml2 PGP(14:0(3-OH)/14:0(3-OH)) + Water >2 PG(14:0(3-OH)/14:0(3-OH)) + PhosphatePW_R005721