2.02015-09-08 19:40:05 -06002016-09-13 16:36:11 -0600ECMDB24544M2MDB006661PGP(19:iso/19:0cycv8c)PGP(19:iso/19:0cycv8c) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(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, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.C44H86O13P2885.107884.554366825[(2S)-3-({[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2S)-3-{[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCCCCC1CC1CCCCCCInChI=1S/C44H86O13P2/c1-4-5-6-24-29-39-33-40(39)30-25-20-16-14-18-22-27-32-44(47)57-42(37-56-59(51,52)55-35-41(45)34-54-58(48,49)50)36-53-43(46)31-26-21-17-13-11-9-7-8-10-12-15-19-23-28-38(2)3/h38-42,45H,4-37H2,1-3H3,(H,51,52)(H2,48,49,50)/t39?,40?,41-,42+/m0/s1GAQFRIUOLARGJR-IXDDWDRSSA-Nlogp7.44logs-6.35solubility3.97e-04 g/llogp12.54pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2S)-3-({[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-[(17-methyloctadecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass885.107mono_mass884.554366825smiles[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCC(C)C)OC(=O)CCCCCCCCCC1CC1CCCCCCformulaC44H86O13P2inchiInChI=1S/C44H86O13P2/c1-4-5-6-24-29-39-33-40(39)30-25-20-16-14-18-22-27-32-44(47)57-42(37-56-59(51,52)55-35-41(45)34-54-58(48,49)50)36-53-43(46)31-26-21-17-13-11-9-7-8-10-12-15-19-23-28-38(2)3/h38-42,45H,4-37H2,1-3H3,(H,51,52)(H2,48,49,50)/t39?,40?,41-,42+/m0/s1inchikeyGAQFRIUOLARGJR-IXDDWDRSSA-Npolar_surface_area195.35refractivity231.83polarizability103.93rotatable_bond_count45acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid 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::NmrOneD316161Specdb::NmrOneD316162Specdb::NmrOneD316163Specdb::NmrOneD316164Specdb::NmrOneD316165Specdb::NmrOneD316166Specdb::NmrOneD316167Specdb::NmrOneD316168Specdb::NmrOneD316169Specdb::NmrOneD316170Specdb::NmrOneD316171Specdb::NmrOneD316172Specdb::NmrOneD316173Specdb::NmrOneD316174Specdb::NmrOneD316175Specdb::NmrOneD316176Specdb::NmrOneD316177Specdb::NmrOneD316178Specdb::NmrOneD316179Specdb::NmrOneD316180Specdb::MsMs25439Specdb::MsMs25440Specdb::MsMs25441Specdb::MsMs31997Specdb::MsMs31998Specdb::MsMs31999Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.APhosphatidylglycerophosphatase BP0A924PGPB_ECOLIpgpBhttp://ecmdb.ca/proteins/P0A924.xmlCDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferaseP0ABF8PGSA_ECOLIpgsAhttp://ecmdb.ca/proteins/P0ABF8.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xml2 CDP-DG(19:iso/19:0cycv8c) + Glycerol 3-phosphate >2 PGP(19:iso/19:0cycv8c) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0056582 PGP(19:iso/19:0cycv8c) + Water >2 PG(19:iso/19:0cycv8c) + PhosphatePW_R005659