2.02012-10-24 09:54:52 -06002015-12-09 12:06:01 -0700ECMDB23638M2MDB004028PG(10:0(3-OH)/15:0cyclo)PG(10:0(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(10:0(3-OH)/15:0cyclo), in particular, consists of one 3-hydroxydecanoyl 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-hydroxydecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho-(1'-glycerol)1-3-hydroxydecanoyl-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phosphoglycerol1-NULL-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phospho-(1'-glycerol)1-NULL-2-(cis-9,10-Methylenetetradecanoyl)-sn-glycero-3-phosphoglycerolGPG(10:0/15:0)GPG(25:0)PG(10:0/15:0)PG(25:0)Phosphatidylglycerol(10:0/15:0)Phosphatidylglycerol(25:0)C31H59O11P638.776638.379499718[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydecanoyl)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)CCCCCCCInChI=1S/C31H59O11P/c1-3-5-7-9-13-17-27(33)20-31(36)42-29(24-41-43(37,38)40-22-28(34)21-32)23-39-30(35)18-14-11-8-10-12-16-26-19-25(26)15-6-4-2/h25-29,32-34H,3-24H2,1-2H3,(H,37,38)/t25?,26?,27?,28-,29+/m0/s1OKIUYVUZRIMBGJ-IFULXZEUSA-NSolidMembranelogp4.37logs-5.86solubility8.79e-04 g/llogp5.82pka_strongest_acidic1.89pka_strongest_basic-2.8iupac[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(3-hydroxydecanoyl)oxy]propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acidaverage_mass638.776mono_mass638.379499718smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CC(O)CCCCCCCformulaC31H59O11PinchiInChI=1S/C31H59O11P/c1-3-5-7-9-13-17-27(33)20-31(36)42-29(24-41-43(37,38)40-22-28(34)21-32)23-39-30(35)18-14-11-8-10-12-16-26-19-25(26)15-6-4-2/h25-29,32-34H,3-24H2,1-2H3,(H,37,38)/t25?,26?,27?,28-,29+/m0/s1inchikeyOKIUYVUZRIMBGJ-IFULXZEUSA-Npolar_surface_area169.05refractivity162.71polarizability71.58rotatable_bond_count31acceptor_count7donor_count4physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(10:0(3-OH)/15:0cyclo/10:0(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.
PW001902MetabolicSpecdb::CMs1084116Specdb::EiMs5082Specdb::NmrOneD271258Specdb::NmrOneD271259Specdb::NmrOneD271260Specdb::NmrOneD271261Specdb::NmrOneD271262Specdb::NmrOneD271263Specdb::NmrOneD271264Specdb::NmrOneD271265Specdb::NmrOneD271266Specdb::NmrOneD271267Specdb::NmrOneD271268Specdb::NmrOneD271269Specdb::NmrOneD271270Specdb::NmrOneD271271Specdb::NmrOneD271272Specdb::NmrOneD271273Specdb::NmrOneD271274Specdb::NmrOneD271275Specdb::NmrOneD271276Specdb::NmrOneD271277Specdb::MsMs1233280Specdb::MsMs1233281Specdb::MsMs1233282Specdb::MsMs1348792Specdb::MsMs1348793Specdb::MsMs1348794Kanehisa, 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-D114.22080510Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-9622753057Yurtsever 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(10:0(3-OH)/15:0cyclo) + Water >2 PG(10:0(3-OH)/15:0cyclo) + PhosphatePW_R0052952 PG(10:0(3-OH)/15:0cyclo) > CL(10:0(3-OH)/15:0cyclo/10:0(3-OH)/15:0cyclo) + GlycerolPW_R005297