2.02012-10-24 09:55:08 -06002015-09-16 17:34:55 -0600ECMDB23726M2MDB004116PG(19:iso/19:iso)PG(19:iso/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(19:iso/19:iso), in particular, consists of two 17-methylocatdecanoyl 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-di17-methylocatdecanoyl-rac-glycero-3-phospho-(1'-glycerol)1,2-di17-methylocatdecanoyl-rac-glycero-3-phosphoglycerol1,2-di17-methylocatdecanoyl-rac-glycero-3-phosphoglycerolGPG(19:0/19:0)GPG(38:0)PG(19:0/19:0)PG(38:0)Phosphatidylglycerol(19:0/19:0)Phosphatidylglycerol(38:0)C44H87O10P807.1293806.603685516{2,3-bis[(17-methyloctadecanoyl)oxy]propoxy}(2,3-dihydroxypropoxy)phosphinic acid2,3-bis[(17-methyloctadecanoyl)oxy]propoxy(2,3-dihydroxypropoxy)phosphinic acidCC(C)CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)CInChI=1S/C44H87O10P/c1-39(2)31-27-23-19-15-11-7-5-9-13-17-21-25-29-33-43(47)51-37-42(38-53-55(49,50)52-36-41(46)35-45)54-44(48)34-30-26-22-18-14-10-6-8-12-16-20-24-28-32-40(3)4/h39-42,45-46H,5-38H2,1-4H3,(H,49,50)SCHGSUATWXZIMH-UHFFFAOYSA-NSolidMembranelogp8.50logs-7.04solubility7.28e-05 g/llogp13.29pka_strongest_acidic1.89pka_strongest_basic-3iupac{2,3-bis[(17-methyloctadecanoyl)oxy]propoxy}(2,3-dihydroxypropoxy)phosphinic acidaverage_mass807.1293mono_mass806.603685516smilesCC(C)CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCCCCC(C)CformulaC44H87O10PinchiInChI=1S/C44H87O10P/c1-39(2)31-27-23-19-15-11-7-5-9-13-17-21-25-29-33-43(47)51-37-42(38-53-55(49,50)52-36-41(46)35-45)54-44(48)34-30-26-22-18-14-10-6-8-12-16-20-24-28-32-40(3)4/h39-42,45-46H,5-38H2,1-4H3,(H,49,50)inchikeySCHGSUATWXZIMH-UHFFFAOYSA-Npolar_surface_area148.82refractivity222.81polarizability100.65rotatable_bond_count44acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(19:iso/19:iso/19:iso/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.PW002009MetabolicSpecdb::CMs1088421Specdb::MsMs28487Specdb::MsMs28488Specdb::MsMs28489Specdb::MsMs35045Specdb::MsMs35046Specdb::MsMs35047Kanehisa, 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.xml2 PGP(19:iso/19:iso) + Water >2 PG(19:iso/19:iso) + PhosphatePW_R0056632 PG(19:iso/19:iso) > Glycerol + CL(19:iso/19:iso/19:iso/19:iso)PW_R005664