2.02012-10-24 09:54:54 -06002015-09-16 17:34:53 -0600ECMDB23648M2MDB004038PG(10:0/19:iso)PG(10:0/19: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(10:0/19:iso), in particular, consists of one decanoyl 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-decanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-decanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol1-decanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerolGPG(10:0/19:0)GPG(29:0)PG(10:0/19:0)PG(29:0)Phosphatidylglycerol(10:0/19:0)Phosphatidylglycerol(29:0)C35H69O10P680.8901680.46283494[3-(decanoyloxy)-2-[(17-methyloctadecanoyl)oxy]propoxy](2,3-dihydroxypropoxy)phosphinic acid3-(decanoyloxy)-2-[(17-methyloctadecanoyl)oxy]propoxy(2,3-dihydroxypropoxy)phosphinic acidCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)CInChI=1S/C35H69O10P/c1-4-5-6-7-15-19-22-25-34(38)42-29-33(30-44-46(40,41)43-28-32(37)27-36)45-35(39)26-23-20-17-14-12-10-8-9-11-13-16-18-21-24-31(2)3/h31-33,36-37H,4-30H2,1-3H3,(H,40,41)URLMNMMAZXYDKP-UHFFFAOYSA-NSolidMembranelogp6.85logs-6.44solubility2.46e-04 g/llogp9.45pka_strongest_acidic1.89pka_strongest_basic-3iupac[3-(decanoyloxy)-2-[(17-methyloctadecanoyl)oxy]propoxy](2,3-dihydroxypropoxy)phosphinic acidaverage_mass680.8901mono_mass680.46283494smilesCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)CformulaC35H69O10PinchiInChI=1S/C35H69O10P/c1-4-5-6-7-15-19-22-25-34(38)42-29-33(30-44-46(40,41)43-28-32(37)27-36)45-35(39)26-23-20-17-14-12-10-8-9-11-13-16-18-21-24-31(2)3/h31-33,36-37H,4-30H2,1-3H3,(H,40,41)inchikeyURLMNMMAZXYDKP-UHFFFAOYSA-Npolar_surface_area148.82refractivity181.45polarizability81.62rotatable_bond_count36acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(19:iso/10:0/19:iso/10:0))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.
PW001998MetabolicSpecdb::CMs1085946Specdb::NmrOneD277078Specdb::NmrOneD277079Specdb::NmrOneD277080Specdb::NmrOneD277081Specdb::NmrOneD277082Specdb::NmrOneD277083Specdb::NmrOneD277084Specdb::NmrOneD277085Specdb::NmrOneD277086Specdb::NmrOneD277087Specdb::NmrOneD277088Specdb::NmrOneD277089Specdb::NmrOneD277090Specdb::NmrOneD277091Specdb::NmrOneD277092Specdb::NmrOneD277093Specdb::NmrOneD277094Specdb::NmrOneD277095Specdb::NmrOneD277096Specdb::NmrOneD277097Specdb::MsMs29078Specdb::MsMs29079Specdb::MsMs29080Specdb::MsMs35636Specdb::MsMs35637Specdb::MsMs35638Kanehisa, 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-D114.22080510Casadei MA, MaƱas 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.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.xmlPGP(16:0/16:0) + Water > PG(10:0/19:iso) + PhosphatePW_R0041482 PG(10:0/19:iso) > Glycerol + CL(19:0cycv8c/14:0/14:0/17:0cycw7c)PW_R0041462 PG(10:0/19:iso) > Glycerol + CL(19:0cycv8c/14:0/17:0cycw7c/14:0)PW_R0041562 PG(10:0/19:iso) > Glycerol + CL(19:0cycv8c/17:0cycw7c/14:0/14:0)PW_R0043102 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/19:0cycv8c/14:0/14:0)PW_R0043912 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/14:0/14:0/18:1(9Z))PW_R0044082 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/14:0/18:1(9Z)/14:0)PW_R0044182 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/16:0/14:0/16:0)PW_R0045032 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/16:1(9Z)/14:0/16:1(9Z))PW_R0045282 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/16:1(9Z)/16:1(9Z)/14:0)PW_R0045322 PG(10:0/19:iso) > Glycerol + CL(18:1(9Z)/18:1(9Z)/14:0/14:0)PW_R0045742 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/16:1(9Z)/14:0/17:0cycw7c)PW_R0046152 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/16:1(9Z)/17:0cycw7c/14:0)PW_R0046192 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/17:0cycw7c/14:0/16:0)PW_R0046292 PG(10:0/19:iso) > Glycerol + CL(17:0cycw7c/17:0cycw7c/14:0/16:1(9Z))PW_R0046302 PGP(10:0/19:iso) + Water >2 PG(10:0/19:iso) + PhosphatePW_R005718