2.02012-10-24 09:55:00 -06002015-12-09 12:06:56 -0700ECMDB23683M2MDB004073PG(14:0/14:0(3-OH))PG(14:0/14:0(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(14:0/14:0(3-OH)), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one 3-hydroxytetradecanoyl 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-myristoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoglycerol1-tetradecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phospho-(1'-glycerol)1-tetradecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoglycerolGPG(14:0/14:0)GPG(28:0)PG(14:0/14:0)PG(28:0)Phosphatidylglycerol(14:0/14:0)Phosphatidylglycerol(28:0)C34H67O11P682.873682.442099975[(2S)-2,3-dihydroxypropoxy][(2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-(tetradecanoyloxy)propoxy]phosphinic acid(2S)-2,3-dihydroxypropoxy((2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-(tetradecanoyloxy)propoxy)phosphinic acid[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCInChI=1S/C34H67O11P/c1-3-5-7-9-11-13-14-16-18-20-22-24-33(38)45-32(29-44-46(40,41)43-27-31(37)26-35)28-42-34(39)25-30(36)23-21-19-17-15-12-10-8-6-4-2/h30-32,35-37H,3-29H2,1-2H3,(H,40,41)/t30?,31-,32+/m0/s1LAXPWKYQIHCMJL-XXWVNBFBSA-NSolidMembranelogp5.77logs-6.06solubility5.94e-04 g/llogp7.93pka_strongest_acidic1.89pka_strongest_basic-2.8iupac[(2S)-2,3-dihydroxypropoxy][(2R)-3-[(3-hydroxytetradecanoyl)oxy]-2-(tetradecanoyloxy)propoxy]phosphinic acidaverage_mass682.873mono_mass682.442099975smiles[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCformulaC34H67O11PinchiInChI=1S/C34H67O11P/c1-3-5-7-9-11-13-14-16-18-20-22-24-33(38)45-32(29-44-46(40,41)43-27-31(37)26-35)28-42-34(39)25-30(36)23-21-19-17-15-12-10-8-6-4-2/h30-32,35-37H,3-29H2,1-2H3,(H,40,41)/t30?,31-,32+/m0/s1inchikeyLAXPWKYQIHCMJL-XXWVNBFBSA-Npolar_surface_area169.05refractivity178.42polarizability80.18rotatable_bond_count36acceptor_count7donor_count4physiological_charge-1formal_charge0Glycerophospholipid metabolismec00564phospholipid biosynthesis (CL(17:0cycw7c/10:0(3-OH)/14:0/14:0))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.
PW001966MetabolicSpecdb::CMs1084716Specdb::NmrOneD253788Specdb::NmrOneD253789Specdb::NmrOneD253790Specdb::NmrOneD253791Specdb::NmrOneD253792Specdb::NmrOneD253793Specdb::NmrOneD253794Specdb::NmrOneD253795Specdb::NmrOneD253796Specdb::NmrOneD253797Specdb::NmrOneD253798Specdb::NmrOneD253799Specdb::NmrOneD253800Specdb::NmrOneD253801Specdb::NmrOneD253802Specdb::NmrOneD253803Specdb::NmrOneD253804Specdb::NmrOneD253805Specdb::NmrOneD253806Specdb::NmrOneD253807Specdb::MsMs1271572Specdb::MsMs1271573Specdb::MsMs1271574Specdb::MsMs1386580Specdb::MsMs1386581Specdb::MsMs1386582Kanehisa, 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(14:0/14:0(3-OH)) + Water >2 PG(14:0/14:0(3-OH)) + PhosphatePW_R005723