2.02015-09-08 19:32:49 -06002015-12-09 17:18:46 -0700ECMDB24443M2MDB006560PGP(12:0/10:0(3-OH))PGP(12:0/10:0(3-OH)) 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(12:0/10:0(3-OH)), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 3-hydroxydecanoyl 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.C28H56O14P2678.69678.314530479[(2R)-3-({[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid(2R)-3-{[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxydecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCInChI=1S/C28H56O14P2/c1-3-5-7-9-10-11-12-14-16-18-27(31)38-22-26(42-28(32)19-24(29)17-15-13-8-6-4-2)23-41-44(36,37)40-21-25(30)20-39-43(33,34)35/h24-26,29-30H,3-23H2,1-2H3,(H,36,37)(H2,33,34,35)/t24?,25-,26-/m1/s1PNCZARHUGNKELX-KPRFIHOGSA-Nlogp2.99logs-4.18solubility4.50e-02 g/llogp5.14pka_strongest_acidic1.35pka_strongest_basic-2.8iupac[(2R)-3-({[(2R)-3-(dodecanoyloxy)-2-[(3-hydroxydecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acidaverage_mass678.69mono_mass678.314530479smiles[H][C@@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCC)OC(=O)CC(O)CCCCCCCformulaC28H56O14P2inchiInChI=1S/C28H56O14P2/c1-3-5-7-9-10-11-12-14-16-18-27(31)38-22-26(42-28(32)19-24(29)17-15-13-8-6-4-2)23-41-44(36,37)40-21-25(30)20-39-43(33,34)35/h24-26,29-30H,3-23H2,1-2H3,(H,36,37)(H2,33,34,35)/t24?,25-,26-/m1/s1inchikeyPNCZARHUGNKELX-KPRFIHOGSA-Npolar_surface_area215.58refractivity161.69polarizability72.77rotatable_bond_count32acceptor_count9donor_count5physiological_charge-3formal_charge0phospholipid biosynthesis (CL(12:0/10:0(3-OH)/12:0/10:0(3-OH)))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.
PW001928MetabolicSpecdb::CMs1085646Specdb::NmrOneD276098Specdb::NmrOneD276099Specdb::NmrOneD276100Specdb::NmrOneD276101Specdb::NmrOneD276102Specdb::NmrOneD276103Specdb::NmrOneD276104Specdb::NmrOneD276105Specdb::NmrOneD276106Specdb::NmrOneD276107Specdb::NmrOneD276108Specdb::NmrOneD276109Specdb::NmrOneD276110Specdb::NmrOneD276111Specdb::NmrOneD276112Specdb::NmrOneD276113Specdb::NmrOneD276114Specdb::NmrOneD276115Specdb::NmrOneD276116Specdb::NmrOneD276117Specdb::MsMs1294609Specdb::MsMs1294610Specdb::MsMs1294611Specdb::MsMs1409266Specdb::MsMs1409267Specdb::MsMs1409268Yurtsever 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(12:0/10:0(3-OH)) + Glycerol 3-phosphate >2 PGP(12:0/10:0(3-OH)) + Cytidine monophosphate + Hydrogen ion + Cytidine monophosphatePW_R0054012 PGP(12:0/10:0(3-OH)) + Water >2 PG(12:0/10:0(3-OH)) + PhosphatePW_R005402