2.02012-10-24 09:54:53 -06002015-12-09 12:06:09 -0700ECMDB23645M2MDB004035PG(10:0/10:0(3-OH))PG(10:0/10:0(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(10:0/10:0(3-OH)), in particular, consists of one decanoyl chain to the C-1 atom, and one 3-hydroxydecanoyl 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-decanoyl-2-3-hydroxydecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-decanoyl-2-3-hydroxydecanoyl-sn-glycero-3-phosphoglycerol1-decanoyl-2-NULL-sn-glycero-3-phospho-(1'-glycerol)1-decanoyl-2-NULL-sn-glycero-3-phosphoglycerolGPG(10:0/10:0)GPG(20:0)PG(10:0/10:0)PG(20:0)Phosphatidylglycerol(10:0/10:0)Phosphatidylglycerol(20:0)C26H51O11P570.657570.31689946[(2R)-2-(decanoyloxy)-3-[(3-hydroxydecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid(2R)-2-(decanoyloxy)-3-[(3-hydroxydecanoyl)oxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCC)OC(=O)CCCCCCCCCInChI=1S/C26H51O11P/c1-3-5-7-9-10-12-14-16-25(30)37-24(21-36-38(32,33)35-19-23(29)18-27)20-34-26(31)17-22(28)15-13-11-8-6-4-2/h22-24,27-29H,3-21H2,1-2H3,(H,32,33)/t22?,23-,24+/m0/s1UBDIMGYIYVMTPA-YDUIRMPASA-NSolidMembranelogp3.14logs-5.25solubility3.18e-03 g/llogp4.37pka_strongest_acidic1.89pka_strongest_basic-2.8iupac[(2R)-2-(decanoyloxy)-3-[(3-hydroxydecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acidaverage_mass570.657mono_mass570.31689946smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCC)OC(=O)CCCCCCCCCformulaC26H51O11PinchiInChI=1S/C26H51O11P/c1-3-5-7-9-10-12-14-16-25(30)37-24(21-36-38(32,33)35-19-23(29)18-27)20-34-26(31)17-22(28)15-13-11-8-6-4-2/h22-24,27-29H,3-21H2,1-2H3,(H,32,33)/t22?,23-,24+/m0/s1inchikeyUBDIMGYIYVMTPA-YDUIRMPASA-Npolar_surface_area169.05refractivity141.61polarizability63.1rotatable_bond_count28acceptor_count7donor_count4physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(10:0/10:0(3-OH)/10:0/10:0(3-OH)))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.PW001910MetabolicSpecdb::CMs1084436Specdb::NmrOneD335798Specdb::NmrOneD335799Specdb::NmrOneD335800Specdb::NmrOneD335801Specdb::NmrOneD335802Specdb::NmrOneD335803Specdb::NmrOneD335804Specdb::NmrOneD335805Specdb::NmrOneD335806Specdb::NmrOneD335807Specdb::NmrOneD335808Specdb::NmrOneD335809Specdb::NmrOneD335810Specdb::NmrOneD335811Specdb::NmrOneD335812Specdb::NmrOneD335813Specdb::NmrOneD335814Specdb::NmrOneD335815Specdb::NmrOneD335816Specdb::NmrOneD335817Specdb::MsMs1328791Specdb::MsMs1328792Specdb::MsMs1328793Specdb::MsMs1443121Specdb::MsMs1443122Specdb::MsMs1443123Kanehisa, 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(10:0/10:0(3-OH)) + Water >2 PG(10:0/10:0(3-OH)) + PhosphatePW_R0053252 PG(10:0/10:0(3-OH)) > Glycerol + CL(10:0/10:0(3-OH)/10:0/10:0(3-OH))PW_R005326