2.02015-09-08 19:35:44 -06002015-12-09 17:20:52 -0700ECMDB24501M2MDB006618PGP(17:0cycw7c/16:1(9Z))PGP(17:0cycw7c/16:1(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(17:0cycw7c/16:1(9Z)), in particular, consists of one heptadec-9-10-cyclo-anoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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.C39H74O13P2812.956812.460466439[(2R)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCInChI=1S/C39H74O13P2/c1-3-5-7-9-10-11-12-13-14-15-16-19-24-28-39(42)52-37(33-51-54(46,47)50-31-36(40)30-49-53(43,44)45)32-48-38(41)27-23-20-17-18-22-26-35-29-34(35)25-21-8-6-4-2/h11-12,34-37,40H,3-10,13-33H2,1-2H3,(H,46,47)(H2,43,44,45)/b12-11-/t34?,35?,36-,37-/m1/s1CBRAARCYPATVPD-ROKAYYDNSA-Nlogp6.61logs-5.95solubility9.02e-04 g/llogp10.12pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2R)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass812.956mono_mass812.460466439smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCformulaC39H74O13P2inchiInChI=1S/C39H74O13P2/c1-3-5-7-9-10-11-12-13-14-15-16-19-24-28-39(42)52-37(33-51-54(46,47)50-31-36(40)30-49-53(43,44)45)32-48-38(41)27-23-20-17-18-22-26-35-29-34(35)25-21-8-6-4-2/h11-12,34-37,40H,3-10,13-33H2,1-2H3,(H,46,47)(H2,43,44,45)/b12-11-/t34?,35?,36-,37-/m1/s1inchikeyCBRAARCYPATVPD-ROKAYYDNSA-Npolar_surface_area195.35refractivity209.99polarizability92.57rotatable_bond_count40acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid biosynthesis CL(16:0/16:0/17:0cycw7c/16:1(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."PW001273MetabolicSpecdb::CMs1085210Specdb::EiMs4168Specdb::NmrOneD248588Specdb::NmrOneD248589Specdb::NmrOneD248590Specdb::NmrOneD248591Specdb::NmrOneD248592Specdb::NmrOneD248593Specdb::NmrOneD248594Specdb::NmrOneD248595Specdb::NmrOneD248596Specdb::NmrOneD248597Specdb::NmrOneD248598Specdb::NmrOneD248599Specdb::NmrOneD248600Specdb::NmrOneD248601Specdb::NmrOneD248602Specdb::NmrOneD248603Specdb::NmrOneD248604Specdb::NmrOneD248605Specdb::NmrOneD248606Specdb::NmrOneD248607Specdb::MsMs1222744Specdb::MsMs1222745Specdb::MsMs1222746Specdb::MsMs1338388Specdb::MsMs1338389Specdb::MsMs1338390Yurtsever 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.xmlPhosphatidylglycerophosphatase AP18200PGPA_ECOLIpgpAhttp://ecmdb.ca/proteins/P18200.xml2 PGP(17:0cycw7c/16:1(9Z)) + Water >2 PG(17:0cycw7c/16:1(9Z)) + PhosphatePW_R005788