2.02012-10-24 09:54:56 -06002015-09-16 17:34:53 -0600ECMDB23662M2MDB004052PG(12:0(3-OH)/19:iso)PG(12:0(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(12:0(3-OH)/19:iso), in particular, consists of one 3-hydroxydodecanoyl 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-hydroxydodecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-3-hydroxydodecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerol1-3-hydroxydodecanoyl-2-17-methylocatdecanoyl-sn-glycero-3-phosphoglycerolGPG(12:0/19:0)GPG(31:0)PG(12:0/19:0)PG(31:0)Phosphatidylglycerol(12:0/19:0)Phosphatidylglycerol(31:0)C37H73O11P724.9427724.48904969(2,3-dihydroxypropoxy)({3-[(3-hydroxydodecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acid2,3-dihydroxypropoxy(3-[(3-hydroxydodecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acidCCCCCCCCCC(O)CC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)CInChI=1S/C37H73O11P/c1-4-5-6-7-15-19-22-25-33(39)27-37(42)45-30-35(31-47-49(43,44)46-29-34(40)28-38)48-36(41)26-23-20-17-14-12-10-8-9-11-13-16-18-21-24-32(2)3/h32-35,38-40H,4-31H2,1-3H3,(H,43,44)IEZZFFDVHDTWPL-UHFFFAOYSA-NSolidMembranelogp6.43logs-6.38solubility3.04e-04 g/llogp9.1pka_strongest_acidic1.89pka_strongest_basic-2.8iupac(2,3-dihydroxypropoxy)({3-[(3-hydroxydodecanoyl)oxy]-2-[(17-methyloctadecanoyl)oxy]propoxy})phosphinic acidaverage_mass724.9427mono_mass724.48904969smilesCCCCCCCCCC(O)CC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)CformulaC37H73O11PinchiInChI=1S/C37H73O11P/c1-4-5-6-7-15-19-22-25-33(39)27-37(42)45-30-35(31-47-49(43,44)46-29-34(40)28-38)48-36(41)26-23-20-17-14-12-10-8-9-11-13-16-18-21-24-32(2)3/h32-35,38-40H,4-31H2,1-3H3,(H,43,44)inchikeyIEZZFFDVHDTWPL-UHFFFAOYSA-Npolar_surface_area169.05refractivity192.17polarizability86.55rotatable_bond_count38acceptor_count7donor_count4physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(12:0(3-OH)/19:iso/12:0(3-OH)/19:iso))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.
PW001926MetabolicSpecdb::CMs1087140Specdb::NmrOneD277098Specdb::NmrOneD277099Specdb::NmrOneD277100Specdb::NmrOneD277101Specdb::NmrOneD277102Specdb::NmrOneD277103Specdb::NmrOneD277104Specdb::NmrOneD277105Specdb::NmrOneD277106Specdb::NmrOneD277107Specdb::NmrOneD277108Specdb::NmrOneD277109Specdb::NmrOneD277110Specdb::NmrOneD277111Specdb::NmrOneD277112Specdb::NmrOneD277113Specdb::NmrOneD277114Specdb::NmrOneD277115Specdb::NmrOneD277116Specdb::NmrOneD277117Specdb::MsMs23534Specdb::MsMs23535Specdb::MsMs23536Specdb::MsMs24224Specdb::MsMs24225Specdb::MsMs24226Specdb::MsMs30332Specdb::MsMs30333Specdb::MsMs30334Kanehisa, 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-D114.22080510Taylor SS, Heath EC. (1969) "The incorporation of beta-hydroxy fatty acids into a phospholipid of Escherichia coli B." J Biol Chem. 244(24):6605-16.4902888Casadei 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.xml2 PGP(12:0(3-OH)/19:iso) + Water >2 PG(12:0(3-OH)/19:iso) + PhosphatePW_R0053982 PG(12:0(3-OH)/19:iso) > Glycerol + CL(12:0(3-OH)/19:iso/12:0(3-OH)/19:iso)PW_R005399