2.02015-09-08 19:37:30 -06002015-12-09 17:21:48 -0700ECMDB24523M2MDB006640PGP(19:0cycv8c/18:1(9Z))PGP(19:0cycv8c/18:1(9Z)) 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(19:0cycv8c/18:1(9Z)), in particular, consists of one heptadec-11-12-cyclo-anoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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.C43H82O13P2869.064868.523066696[(2R)-3-({[(2R)-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-2-[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-2-[(9Z)-octadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCCInChI=1S/C43H82O13P2/c1-3-5-7-9-10-11-12-13-14-15-16-17-20-24-28-32-43(46)56-41(37-55-58(50,51)54-35-40(44)34-53-57(47,48)49)36-52-42(45)31-27-23-21-18-19-22-26-30-39-33-38(39)29-25-8-6-4-2/h13-14,38-41,44H,3-12,15-37H2,1-2H3,(H,50,51)(H2,47,48,49)/b14-13-/t38?,39?,40-,41-/m1/s1DYQYEICZGKIDND-ZGLIQWPXSA-Nlogp7.44logs-6.27solubility4.62e-04 g/llogp11.9pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2R)-3-({[(2R)-3-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-2-[(9Z)-octadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass869.064mono_mass868.523066696smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCCformulaC43H82O13P2inchiInChI=1S/C43H82O13P2/c1-3-5-7-9-10-11-12-13-14-15-16-17-20-24-28-32-43(46)56-41(37-55-58(50,51)54-35-40(44)34-53-57(47,48)49)36-52-42(45)31-27-23-21-18-19-22-26-30-39-33-38(39)29-25-8-6-4-2/h13-14,38-41,44H,3-12,15-37H2,1-2H3,(H,50,51)(H2,47,48,49)/b14-13-/t38?,39?,40-,41-/m1/s1inchikeyDYQYEICZGKIDND-ZGLIQWPXSA-Npolar_surface_area195.35refractivity228.4polarizability101.02rotatable_bond_count44acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid biosynthesis (CL(19:0cycv8c/18:1(9Z)/14:0/18:1(9Z)))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.PW001415Metabolicphospholipid biosynthesis (CL(19:0cycv8c/18:1(9Z)/17:0cycw7c/17:0cycw7c))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.PW001422MetabolicSpecdb::EiMs2232Specdb::MsMs1271053Specdb::MsMs1271054Specdb::MsMs1271055Specdb::MsMs1386061Specdb::MsMs1386062Specdb::MsMs1386063Yurtsever 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(19:0cycv8c/18:1(9Z)) + Glycerol 3-phosphate >2 PGP(19:0cycv8c/18:1(9Z)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R005262PGP(19:0cycv8c/18:1(9Z)) + Water > PG(19:0cycv8c/18:1(9Z)) + PhosphatePW_R005261