2.02012-10-24 09:54:55 -06002015-12-09 12:06:24 -0700ECMDB23656M2MDB004046PG(12:0(3-OH)/15:0cyclo)PG(12:0(3-OH)/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(12:0(3-OH)/15:0cyclo), in particular, consists of one 3-hydroxydodecanoyl 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.1-3-hydroxydodecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho-(1'-glycerol)1-3-hydroxydodecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phosphoglycerol1-3-hydroxydodecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phosphoglycerolGPG(12:0/15:0)GPG(27:0)PG(12:0/15:0)PG(27:0)Phosphatidylglycerol(12:0/15:0)Phosphatidylglycerol(27:0)C33H63O11P666.83666.410799847[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydodecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydodecanoyl)oxy]propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CC(O)CCCCCCCCCInChI=1S/C33H63O11P/c1-3-5-7-8-9-12-15-19-29(35)22-33(38)44-31(26-43-45(39,40)42-24-30(36)23-34)25-41-32(37)20-16-13-10-11-14-18-28-21-27(28)17-6-4-2/h27-31,34-36H,3-26H2,1-2H3,(H,39,40)/t27?,28?,29?,30-,31+/m0/s1RKRSSXLZASRFAF-AIMSBCCHSA-NSolidMembranelogp4.97logs-5.97solubility7.14e-04 g/llogp6.7pka_strongest_acidic1.89pka_strongest_basic-2.8iupac[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydodecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acidaverage_mass666.83mono_mass666.410799847smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CC(O)CCCCCCCCCformulaC33H63O11PinchiInChI=1S/C33H63O11P/c1-3-5-7-8-9-12-15-19-29(35)22-33(38)44-31(26-43-45(39,40)42-24-30(36)23-34)25-41-32(37)20-16-13-10-11-14-18-28-21-27(28)17-6-4-2/h27-31,34-36H,3-26H2,1-2H3,(H,39,40)/t27?,28?,29?,30-,31+/m0/s1inchikeyRKRSSXLZASRFAF-AIMSBCCHSA-Npolar_surface_area169.05refractivity171.91polarizability75.91rotatable_bond_count33acceptor_count7donor_count4physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(12:0(3-OH)/15:0cyclo/12:0(3-OH)/15:0cyclo))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.
PW001921MetabolicSpecdb::CMs1088072Specdb::EiMs3388Specdb::MsMs1235167Specdb::MsMs1235168Specdb::MsMs1235169Specdb::MsMs1350652Specdb::MsMs1350653Specdb::MsMs1350654Kanehisa, 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(3-OH)/15:0cyclo) + Water >2 PG(12:0(3-OH)/15:0cyclo) + PhosphatePW_R0053762 PG(12:0(3-OH)/15:0cyclo) > Glycerol + CL(12:0(3-OH)/15:0cyclo/12:0(3-OH)/15:0cyclo)PW_R005377