2.02012-10-24 09:55:07 -06002015-09-16 17:34:55 -0600ECMDB23720M2MDB004110PG(19:iso/15:0cyclo)PG(19:iso/15:0cyclo) 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/15:0cyclo), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one cis-9,10-Methylenetetradecanoic acid 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.1-17-methylocatdecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho-(1'-glycerol)1-17-methylocatdecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phosphoglycerolGPG(19:0/15:0)GPG(34:0)PG(19:0/15:0)PG(34:0)Phosphatidylglycerol(19:0/15:0)Phosphatidylglycerol(34:0)C40H77O10P749.0071748.525435196(2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy)(2,3-dihydroxypropoxy)phosphinic acid2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy(2,3-dihydroxypropoxy)phosphinic acidCCCCC1CC1CCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)COInChI=1S/C40H77O10P/c1-4-5-25-35-29-36(35)26-21-17-15-19-23-28-40(44)50-38(33-49-51(45,46)48-31-37(42)30-41)32-47-39(43)27-22-18-14-12-10-8-6-7-9-11-13-16-20-24-34(2)3/h34-38,41-42H,4-33H2,1-3H3,(H,45,46)ZNLKIYGIWMJQFS-UHFFFAOYSA-NSolidMembranelogp7.62logs-6.83solubility1.10e-04 g/llogp10.89pka_strongest_acidic1.89pka_strongest_basic-3iupac(2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy)(2,3-dihydroxypropoxy)phosphinic acidaverage_mass749.0071mono_mass748.525435196smilesCCCCC1CC1CCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)COformulaC40H77O10PinchiInChI=1S/C40H77O10P/c1-4-5-25-35-29-36(35)26-21-17-15-19-23-28-40(44)50-38(33-49-51(45,46)48-31-37(42)30-41)32-47-39(43)27-22-18-14-12-10-8-6-7-9-11-13-16-20-24-34(2)3/h34-38,41-42H,4-33H2,1-3H3,(H,45,46)inchikeyZNLKIYGIWMJQFS-UHFFFAOYSA-Npolar_surface_area148.82refractivity202.55polarizability90.62rotatable_bond_count39acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/14:0/19:0cycv8c))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.PW001291MetabolicSpecdb::CMs1087101Specdb::EiMs3208Specdb::NmrOneD269198Specdb::NmrOneD269199Specdb::NmrOneD269200Specdb::NmrOneD269201Specdb::NmrOneD269202Specdb::NmrOneD269203Specdb::NmrOneD269204Specdb::NmrOneD269205Specdb::NmrOneD269206Specdb::NmrOneD269207Specdb::NmrOneD269208Specdb::NmrOneD269209Specdb::NmrOneD269210Specdb::NmrOneD269211Specdb::NmrOneD269212Specdb::NmrOneD269213Specdb::NmrOneD269214Specdb::NmrOneD269215Specdb::NmrOneD269216Specdb::NmrOneD269217Specdb::MsMs23456Specdb::MsMs23457Specdb::MsMs23458Specdb::MsMs24203Specdb::MsMs24204Specdb::MsMs24205Specdb::MsMs30254Specdb::MsMs30255Specdb::MsMs30256Kanehisa, 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.xmlCardiolipin synthase CP75919CLSC_ECOLIclsChttp://ecmdb.ca/proteins/P75919.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.xmlPE(14:0(3-OH)/19:0cycv8c) + PG(19:iso/15:0cyclo) > Ethanolamine + CL(19:0cycv8c/15:0cyclo/14:0/19:0cycv8c)PW_R0049532 PGP(19:iso/15:0cyclo) + Water >2 PG(19:iso/15:0cyclo) + PhosphatePW_R005757