2.02012-10-24 09:54:57 -06002015-12-09 12:06:32 -0700ECMDB23664M2MDB004054PG(12:0/12:0(3-OH))PG(12:0/12:0(3-OH)) 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(12:0/12:0(3-OH)), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 3-hydroxydodecanoyl 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-dodecanoyl-2-3-hydroxydodecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-dodecanoyl-2-3-hydroxydodecanoyl-sn-glycero-3-phosphoglycerol1-dodecanoyl-2-3-hydroxydodecanoyl-sn-glycero-3-phosphoglycerolGPG(12:0/12:0)GPG(24:0)PG(12:0/12:0)PG(24:0)Phosphatidylglycerol(12:0/12:0)Phosphatidylglycerol(24:0)C30H59O11P626.765626.379499718[(2S)-2,3-dihydroxypropoxy][(2R)-2-(dodecanoyloxy)-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy((2R)-2-(dodecanoyloxy)-3-[(3-hydroxydodecanoyl)oxy]propoxy)phosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCCCCCCInChI=1S/C30H59O11P/c1-3-5-7-9-11-12-14-16-18-20-29(34)41-28(25-40-42(36,37)39-23-27(33)22-31)24-38-30(35)21-26(32)19-17-15-13-10-8-6-4-2/h26-28,31-33H,3-25H2,1-2H3,(H,36,37)/t26?,27-,28+/m0/s1FMVLSWAYCHIRMK-GUQXXGRISA-NSolidMembranelogp4.47logs-5.65solubility1.42e-03 g/llogp6.15pka_strongest_acidic1.89pka_strongest_basic-2.8iupac[(2S)-2,3-dihydroxypropoxy][(2R)-2-(dodecanoyloxy)-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acidaverage_mass626.765mono_mass626.379499718smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCCCCCCformulaC30H59O11PinchiInChI=1S/C30H59O11P/c1-3-5-7-9-11-12-14-16-18-20-29(34)41-28(25-40-42(36,37)39-23-27(33)22-31)24-38-30(35)21-26(32)19-17-15-13-10-8-6-4-2/h26-28,31-33H,3-25H2,1-2H3,(H,36,37)/t26?,27-,28+/m0/s1inchikeyFMVLSWAYCHIRMK-GUQXXGRISA-Npolar_surface_area169.05refractivity160.02polarizability71.69rotatable_bond_count32acceptor_count7donor_count4physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(12:0(3-OH)/12:0(3-OH)/12:0/12:0))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.
PW001915MetabolicSpecdb::CMs1085540Specdb::NmrOneD246268Specdb::NmrOneD246269Specdb::NmrOneD246270Specdb::NmrOneD246271Specdb::NmrOneD246272Specdb::NmrOneD246273Specdb::NmrOneD246274Specdb::NmrOneD246275Specdb::NmrOneD246276Specdb::NmrOneD246277Specdb::NmrOneD246278Specdb::NmrOneD246279Specdb::NmrOneD246280Specdb::NmrOneD246281Specdb::NmrOneD246282Specdb::NmrOneD246283Specdb::NmrOneD246284Specdb::NmrOneD246285Specdb::NmrOneD246286Specdb::NmrOneD246287Specdb::MsMs1231243Specdb::MsMs1231244Specdb::MsMs1231245Specdb::MsMs1346779Specdb::MsMs1346780Specdb::MsMs1346781Kanehisa, 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):6605-16.4902888Yurtsever 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(12:0/12:0(3-OH)) + Water >2 PG(12:0/12:0(3-OH)) + PhosphatePW_R005763