2.02015-09-08 19:34:59 -06002015-12-09 17:20:15 -0700ECMDB24487M2MDB006604PGP(16:0/19:0cycw8c)PGP(16:0/19:0cycw8c) 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(16:0/19:0cycw8c), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9-(2-heptylcyclopropyl)nonanoyl 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.C41H80O13P2843.026842.507416632[(2R)-3-({[(2R)-2-{[9-(2-heptylcyclopropyl)nonanoyl]oxy}-3-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-2-{[9-(2-heptylcyclopropyl)nonanoyl]oxy}-3-(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCC1CC1CCCCCCCInChI=1S/C41H80O13P2/c1-3-5-7-9-10-11-12-13-14-15-16-21-25-29-40(43)50-34-39(35-53-56(48,49)52-33-38(42)32-51-55(45,46)47)54-41(44)30-26-22-18-17-20-24-28-37-31-36(37)27-23-19-8-6-4-2/h36-39,42H,3-35H2,1-2H3,(H,48,49)(H2,45,46,47)/t36?,37?,38-,39-/m1/s1LGAOFHRGHDLETM-XFULWAJRSA-Nlogp7.08logs-6.14solubility6.11e-04 g/llogp11.37pka_strongest_acidic1.35pka_strongest_basic-3.4iupac[(2R)-3-({[(2R)-2-{[9-(2-heptylcyclopropyl)nonanoyl]oxy}-3-(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass843.026mono_mass842.507416632smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCC1CC1CCCCCCCformulaC41H80O13P2inchiInChI=1S/C41H80O13P2/c1-3-5-7-9-10-11-12-13-14-15-16-21-25-29-40(43)50-34-39(35-53-56(48,49)52-33-38(42)32-51-55(45,46)47)54-41(44)30-26-22-18-17-20-24-28-37-31-36(37)27-23-19-8-6-4-2/h36-39,42H,3-35H2,1-2H3,(H,48,49)(H2,45,46,47)/t36?,37?,38-,39-/m1/s1inchikeyLGAOFHRGHDLETM-XFULWAJRSA-Npolar_surface_area195.35refractivity218.08polarizability98.44rotatable_bond_count43acceptor_count8donor_count4physiological_charge-3formal_charge0phospholipid biosynthesis (CL(19:0cycv8c/16:0/14:0/14:0))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.PW001320MetabolicSpecdb::EiMs2256Specdb::NmrOneD275838Specdb::NmrOneD275839Specdb::NmrOneD275840Specdb::NmrOneD275841Specdb::NmrOneD275842Specdb::NmrOneD275843Specdb::NmrOneD275844Specdb::NmrOneD275845Specdb::NmrOneD275846Specdb::NmrOneD275847Specdb::NmrOneD275848Specdb::NmrOneD275849Specdb::NmrOneD275850Specdb::NmrOneD275851Specdb::NmrOneD275852Specdb::NmrOneD275853Specdb::NmrOneD275854Specdb::NmrOneD275855Specdb::NmrOneD275856Specdb::NmrOneD275857Specdb::MsMs1262944Specdb::MsMs1262945Specdb::MsMs1262946Specdb::MsMs1378039Specdb::MsMs1378040Specdb::MsMs1378041Yurtsever 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(16:0/19:0cycw8c) + Water >2 PG(16:0/19:0cycw8c) + PhosphatePW_R005739