2.02012-08-13 14:57:46 -06002015-09-14 11:19:25 -0600ECMDB21599M2MDB001993PE(12:0/10:0)PE(12:0/10:0) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms. PE(12:0/10:0), in particular, consists of one dodecanoyl chain to the C-1 atom, and one decanoyl to the C-2 atom. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.1-dodecanoyl-2-decanoyl-sn-glycero-3-phosphoethanolamine1-dodecanoyl-2-decanoyl-sn-glycero-3-phosphoethanolamineGPEtn(12:0/10:0)GPEtn(22:0)PE(22:0)Phophatidylethanolamine(12:0/10:0)Phophatidylethanolamine(22:0)C27H54NO8P551.6933551.358704221(2-aminoethoxy)[(2R)-2-(decanoyloxy)-3-(dodecanoyloxy)propoxy]phosphinic acid2-aminoethoxy((2R)-2-(decanoyloxy)-3-(dodecanoyloxy)propoxy)phosphinic acid[H][C@@](COC(=O)CCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCInChI=1S/C27H54NO8P/c1-3-5-7-9-11-12-14-15-17-19-26(29)33-23-25(24-35-37(31,32)34-22-21-28)36-27(30)20-18-16-13-10-8-6-4-2/h25H,3-24,28H2,1-2H3,(H,31,32)/t25-/m1/s1GFVZVLNRUBXMQX-RUZDIDTESA-NSolidMembranelogp5.47logs-5.75solubility9.83e-04 g/llogp6.01pka_strongest_acidic1.87pka_strongest_basic10iupac(2-aminoethoxy)[(2R)-2-(decanoyloxy)-3-(dodecanoyloxy)propoxy]phosphinic acidaverage_mass551.6933mono_mass551.358704221smiles[H][C@@](COC(=O)CCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCformulaC27H54NO8PinchiInChI=1S/C27H54NO8P/c1-3-5-7-9-11-12-14-15-17-19-26(29)33-23-25(24-35-37(31,32)34-22-21-28)36-27(30)20-18-16-13-10-8-6-4-2/h25H,3-24,28H2,1-2H3,(H,31,32)/t25-/m1/s1inchikeyGFVZVLNRUBXMQX-RUZDIDTESA-Npolar_surface_area134.38refractivity144.99polarizability63.81rotatable_bond_count29acceptor_count5donor_count2physiological_charge0formal_charge0Lipopolysaccharide biosynthesisE. coli lipid A is synthesized on the cytoplasmic surface of the inner membrane. The pathway can start from the fructose 6-phosphate that is either produced in the glycolysis and pyruvate dehydrogenase or be obtained from the interaction with D-fructose interacting with a mannose PTS permease. Fructose 6-phosphate interacts with L-glutamine through a D-fructose-6-phosphate aminotransferase resulting into a L-glutamic acid and a glucosamine 6-phosphate. The latter compound is isomerized through a phosphoglucosamine mutase resulting a glucosamine 1-phosphate. This compound is acetylated, interacting with acetyl-CoA through a bifunctional protein glmU resulting in a Coenzyme A, hydrogen ion and N-acetyl-glucosamine 1-phosphate. This compound interact with UTP and hydrogen ion through the bifunctional protein glmU resulting in a pyrophosphate and a UDP-N-acetylglucosamine. This compound interacts with (3R)-3-hydroxymyristoyl-[acp] through an UDP-N-acetylglucosamine acyltransferase resulting in a holo-[acp] and a UDP-3-O[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine. This compound interacts with water through UDP-3-O-acyl-N-acetylglucosamine deacetylase resulting in an acetic acid and UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine. The latter compound interacts with (3R)-3-hydroxymyristoyl-[acp] through
UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase releasing a hydrogen ion, a holo-acp and UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine. The latter compound is hydrolase by interacting with water and a UDP-2,3-diacylglucosamine hydrolase resulting in UMP, hydrogen ion and 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate. This last compound then interacts with a UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine through a lipid A disaccharide synthase resulting in a release of UDP, hydrogen ion and a lipid A disaccharide. The lipid A disaccharide is phosphorylated by an ATP mediated
tetraacyldisaccharide 4'-kinase resulting in the release of hydrogen ion and lipid IVA.
A D-ribulose 5-phosphate is isomerized with D-arabinose 5-phosphate isomerase 2 to result in a D-arabinose 5-phosphate. This compounds interacts with water and phosphoenolpyruvic acid through a 3-deoxy-D-manno-octulosonate 8-phosphate synthase resulting in the release of phosphate and 3-deoxy-D-manno-octulosonate 8-phosphate. This compound interacts with water through a 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase thus releasing a phosphate and a 3-deoxy-D-manno-octulosonate. The latter compound interacts with CTP through a 3-deoxy-D-manno-octulosonate cytidylyltransferase resulting in a pyrophosphate and
CMP-3-deoxy-α-D-manno-octulosonate.
CMP-3-deoxy-α-D-manno-octulosonate and lipid IVA interact with each other through a KDO transferase resulting in CMP, hydrogen ion and alpha-Kdo-(2-->6)-lipid IVA. The latter compound reacts with CMP-3-deoxy-α-D-manno-octulosonate through a KDO transferase resulting in a CMP, hydrogen ion, and a a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA. The latter compound interacts with a dodecanoyl-[acp] lauroyl acyltransferase resulting in a holo-[acp] and a (KDO)2-(lauroyl)-lipid IVA. The latter compound reacts with a myristoyl-[acp] through a myristoyl-acyl carrier protein (ACP)-dependent acyltransferase resulting in a holo-[acp], (KDO)2-lipid A. The latter compound reacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase I resulting hydrogen ion, ADP, heptosyl-KDO2-lipid A. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase II resulting in ADP, hydrogen ion and (heptosyl)2-Kdo2-lipid A. The latter compound UDP-glucose interacts with (heptosyl)2-Kdo2-lipid A resulting in UDP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A. Glucosyl-(heptosyl)2-Kdo2-lipid A (Escherichia coli) is phosphorylated through an ATP-mediated lipopolysaccharide core heptose (I) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate.
The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core heptosyl transferase III resulting in ADP, hydrogen ion, and glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate. The latter compound is phosphorylated through an ATP-driven lipopolysaccharide core heptose (II) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-alpha-D-galactose through a UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase resulting in a UDP, a hydrogen ion and a galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-glucose through a (glucosyl)LPS α-1,3-glucosyltransferase resulting in a hydrogen ion, a UDP and galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with UDP-glucose through a UDP-glucose:(glucosyl)LPS α-1,2-glucosyltransferase resulting in UDP, a hydrogen ion and galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core biosynthesis; heptosyl transferase IV; probably hexose transferase resulting in a Lipid A-core.
A lipid A-core is then exported into the periplasmic space by a lipopolysaccharide ABC transporter.
The lipid A-core is then flipped to the outer surface of the inner membrane by the ATP-binding cassette (ABC) transporter, MsbA. An additional integral membrane protein, YhjD, has recently been implicated in LPS export across the IM. The smallest LPS derivative that supports viability in E. coli is lipid IVA. However, it requires mutations in either MsbA or YhjD, to suppress the normally lethal consequence of an incomplete lipid A . Recent studies with deletion mutants implicate the periplasmic protein LptA, the cytosolic protein LptB, and the IM proteins LptC, LptF, and LptG in the subsequent transport of nascent LPS to the outer membrane (OM), where the LptD/LptE complex flips LPS to the outer surface. PW000831ec00540MetabolicGlycerophospholipid metabolismec00564phospholipid biosynthesis CDP-DG(12:0/10:0) IIPhospholipids 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 PS (16:1(9z)/18:1(11z))L-1-phosphatidylserine or a L-1-phosphatidy PE(16:1(9z)/18:1(11z)) (phosphatidylethanolamine) through a phosphatidylserine decarboxylase, on the other hand PGP(16:1(9z)/18:1(11z)) L-1-phosphatidylglycerol-phosphate gets transformed into a PG(16:1(9z)/18:1(11z)) 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.PW001834Metabolicphospholipid biosynthesis IPHOSLIPSYN-PWYSpecdb::CMs1089194Specdb::NmrOneD342168Specdb::NmrOneD342169Specdb::NmrOneD342170Specdb::NmrOneD342171Specdb::NmrOneD342172Specdb::NmrOneD342173Specdb::NmrOneD342174Specdb::NmrOneD342175Specdb::NmrOneD342176Specdb::NmrOneD342177Specdb::NmrOneD342178Specdb::NmrOneD342179Specdb::NmrOneD342180Specdb::NmrOneD342181Specdb::NmrOneD342182Specdb::NmrOneD342183Specdb::NmrOneD342184Specdb::NmrOneD342185Specdb::NmrOneD342186Specdb::NmrOneD342187Specdb::MsMs29705Specdb::MsMs29706Specdb::MsMs29707Specdb::MsMs36263Specdb::MsMs36264Specdb::MsMs36265Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510De Siervo, A. J. (1969). "Alterations in the phospholipid composition of Escherichia coli B during growth at different temperatures." J Bacteriol 100:1342-1349.4902814Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.APhosphatidylserine decarboxylase proenzymeP0A8K1PSD_ECOLIpsdhttp://ecmdb.ca/proteins/P0A8K1.xmlBifunctional protein aasP31119AAS_ECOLIaashttp://ecmdb.ca/proteins/P31119.xmlPhosphoethanolamine transferase eptBP37661EPTB_ECOLIeptBhttp://ecmdb.ca/proteins/P37661.xmlProtein crcAP37001CRCA_ECOLIcrcAhttp://ecmdb.ca/proteins/P37001.xmlProbable phospholipid ABC transporter-binding protein mlaBP64602MLAB_ECOLImlaBhttp://ecmdb.ca/proteins/P64602.xmlProbable phospholipid ABC transporter-binding protein mlaDP64604MLAD_ECOLImlaDhttp://ecmdb.ca/proteins/P64604.xmlProbable phospholipid ABC transporter permease protein mlaEP64606MLAE_ECOLImlaEhttp://ecmdb.ca/proteins/P64606.xmlPS(12:0(3-OH)/10:0(3-OH)) + Hydrogen ion > PE(12:0/10:0) + Carbon dioxidePW_R004874a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + PE(12:0/10:0) + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > 1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + phosphoethanolamine-Kdo2-lipid A + Phosphoethanolamine KDO(2)-lipid (A)PW_R005296