2.02012-10-24 09:55:08 -06002015-09-16 17:34:55 -0600ECMDB23725M2MDB004115PG(19:iso/19:0cycv8c)PG(19:iso/19:0cycv8c) 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/19:0cycv8c), in particular, consists of one 17-methylocatdecanoyl chain to the C-1 atom, and one heptadec-11-12-cyclo-anoyl 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-(heptadec-11-12-cyclo-anoyl)-sn-glycero-3-phospho-(1'-glycerol)1-17-methylocatdecanoyl-2-(heptadec-11-12-cyclo-anoyl)-sn-glycero-3-phosphoglycerol1-17-methylocatdecanoyl-2-heptadec-11-12-cyclo-anoyl-sn-glycero-3-phospho-(1'-glycerol)1-17-methylocatdecanoyl-2-heptadec-11-12-cyclo-anoyl-sn-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)C44H85O10P805.1135804.588035452(2,3-dihydroxypropoxy)(2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acid2,3-dihydroxypropoxy(2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acidCCCCCCC1CC1CCCCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)COInChI=1S/C44H85O10P/c1-4-5-6-24-29-39-33-40(39)30-25-20-16-14-18-22-27-32-44(48)54-42(37-53-55(49,50)52-35-41(46)34-45)36-51-43(47)31-26-21-17-13-11-9-7-8-10-12-15-19-23-28-38(2)3/h38-42,45-46H,4-37H2,1-3H3,(H,49,50)QWIRCNVQIVUXTH-UHFFFAOYSA-NSolidMembranelogp8.52logs-7.04solubility7.32e-05 g/llogp12.67pka_strongest_acidic1.89pka_strongest_basic-3iupac(2,3-dihydroxypropoxy)(2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy)phosphinic acidaverage_mass805.1135mono_mass804.588035452smilesCCCCCCC1CC1CCCCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCCC(C)C)COP(O)(=O)OCC(O)COformulaC44H85O10PinchiInChI=1S/C44H85O10P/c1-4-5-6-24-29-39-33-40(39)30-25-20-16-14-18-22-27-32-44(48)54-42(37-53-55(49,50)52-35-41(46)34-45)36-51-43(47)31-26-21-17-13-11-9-7-8-10-12-15-19-23-28-38(2)3/h38-42,45-46H,4-37H2,1-3H3,(H,49,50)inchikeyQWIRCNVQIVUXTH-UHFFFAOYSA-Npolar_surface_area148.82refractivity220.96polarizability99rotatable_bond_count43acceptor_count6donor_count3physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(18:1(9Z)/14:0/19:0cycv8c/19:0cycv8c) 2)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.PW001781Metabolicphospholipid biosynthesis (CL(19:iso/19:0cycv8c/19:0/19:0))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.PW002008MetabolicSpecdb::CMs1085978Specdb::NmrOneD344068Specdb::NmrOneD344069Specdb::NmrOneD344070Specdb::NmrOneD344071Specdb::NmrOneD344072Specdb::NmrOneD344073Specdb::NmrOneD344074Specdb::NmrOneD344075Specdb::NmrOneD344076Specdb::NmrOneD344077Specdb::NmrOneD344078Specdb::NmrOneD344079Specdb::NmrOneD344080Specdb::NmrOneD344081Specdb::NmrOneD344082Specdb::NmrOneD344083Specdb::NmrOneD344084Specdb::NmrOneD344085Specdb::NmrOneD344086Specdb::NmrOneD344087Specdb::MsMs29081Specdb::MsMs29082Specdb::MsMs29083Specdb::MsMs35639Specdb::MsMs35640Specdb::MsMs35641Kanehisa, 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.xmlPG(19:iso/19:0cycv8c) + PE(18:1(9Z)/14:0) > Ethanolamine + CL(18:1(9Z)/14:0/19:0cycv8c/19:0cycv8c)PW_R0047702 PGP(19:iso/19:0cycv8c) + Water >2 PG(19:iso/19:0cycv8c) + PhosphatePW_R005659PG(19:iso/19:0cycv8c) + PE(19:0/19:0) > Ethanolamine + CL(19:iso/19:0cycv8c/19:0/19:0)PW_R005660