2.0 2012-07-30 14:55:24 -0600 2015-09-18 09:17:49 -0600 ECMDB21352 M2MDB001750 Phosphoethanolamine KDO(2)-lipid (A) Phosphoethanolamine kdo(2)-lipid (a) belongs to the class of Polysaccharide Phosphates. These are polysaccharides in which a phosphate group is bound to at least one carbohydrate unit. (inferred from compound structure) (2R,4R,5R,6S)-6-(1R)-1-2-azaniumylethoxy(oxido)phosphoryloxy-2-hydroxyethyl-2-(2R,4R,5R,6R)-2-carboxylato-6-(1R)-1,2-dihydroxyethyl-2-(2R,3S,4R,5R,6R)-5-(3R)-3-dodecanoyloxytetradecanoylamino-6-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonatooxyoxan-2-ylmethoxy-3-phosphonatooxy-4-(3R)-3-tetradecanoyloxytetradecanoyloxyoxan-2-ylmethoxy-5-hydroxyoxan-4-yloxy-4,5-dihydroxyoxane-2-carboxylate (2R,4R,5R,6S)-6-(1R)-1-2-Azaniumylethoxy(oxido)phosphoryloxy-2-hydroxyethyl-2-(2R,4R,5R,6R)-2-carboxylato-6-(1R)-1,2-dihydroxyethyl-2-(2R,3S,4R,5R,6R)-5-(3R)-3-dodecanoyloxytetradecanoylamino-6-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonatooxyoxan-2-ylmethoxy-3-phosphonatooxy-4-(3R)-3-tetradecanoyloxytetradecanoyloxyoxan-2-ylmethoxy-5-hydroxyoxan-4-yloxy-4,5-dihydroxyoxane-2-carboxylic acid (6S)-6-(1R)-1-{(2-ammonioethoxy)phosphinatooxy}-2-hydroxyethyl-3-deoxy-b-L-erythro-hex-2-ulopyranonosyl-(2->4)-(6R)-3-deoxy-6-(1R)-1,2-dihydroxyethyl-b-L-erythro-hex-2-ulopyranonosyl-(2->6 )-2-deoxy-2-{(3R)-3-(dodecanoyloxy)tetradecanoylamino}-4-O-phosphonato-3-O-(3R)-3-(tetradecanoyloxy)tetradecanoyl-b-D-glucopyranosyl-(1->6)-2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3- hydroxytetradecanoylamino}-1-O-phosphonato-a-D-glucopyranose (6S)-6-(1R)-1-{(2-Ammonioethoxy)phosphinatooxy}-2-hydroxyethyl-3-deoxy-beta-L-erythro-hex-2-ulopyranonosyl-(2->4)-(6R)-3-deoxy-6-(1R)-1,2-dihydroxyethyl-beta-L-erythro-hex-2-ulopyranonosyl-(2->6 )-2-deoxy-2-{(3R)-3-(dodecanoyloxy)tetradecanoylamino}-4-O-phosphonato-3-O-(3R)-3-(tetradecanoyloxy)tetradecanoyl-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3- hydroxytetradecanoylamino}-1-O-phosphonato-alpha-D-glucopyranose (6S)-6-(1R)-1-{(2-ammonioethoxy)phosphinatooxy}-2-hydroxyethyl-3-deoxy-β-L-erythro-hex-2-ulopyranonosyl-(2->4)-(6R)-3-deoxy-6-(1R)-1,2-dihydroxyethyl-β-L-erythro-hex-2-ulopyranonosyl-(2->6 )-2-deoxy-2-{(3R)-3-(dodecanoyloxy)tetradecanoylamino}-4-O-phosphonato-3-O-(3R)-3-(tetradecanoyloxy)tetradecanoyl-β-D-glucopyranosyl-(1->6)-2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3- hydroxytetradecanoylamino}-1-O-phosphonato-α-D-glucopyranose Phosphoethanolamine-Kdo2-lipid A Phosphoethanolamine-Kdo2-lipid A hexaanion C112H199N3O42P3 2352.728 2351.277394933 (2-{[1-(6-carboxylato-6-{[2-carboxylato-6-(1,2-dihydroxyethyl)-2-({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl}methoxy)-5-hydroxyoxan-4-yl]oxy}-3,4-dihydroxyoxan-2-yl)-2-hydroxyethyl phosphonato]oxy}ethyl)azaniumyl (2-{[1-(6-carboxylato-6-{[2-carboxylato-6-(1,2-dihydroxyethyl)-2-({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl}methoxy)-5-hydroxyoxan-4-yl]oxy}-3,4-dihydroxyoxan-2-yl)-2-hydroxyethyl phosphonato]oxy}ethyl)ammonio CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)C(OCC2OC(OP([O-])([O-])=O)C(NC(=O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)OC(COC2(CC(OC3(CC(O)C(O)C(O3)C(CO)OP([O-])(=O)OCC[N+])C([O-])=O)C(O)C(O2)C(O)CO)C([O-])=O)C1OP([O-])([O-])=O InChI=1S/C112H206N3O42P3/c1-7-13-19-25-31-37-38-44-50-56-62-68-94(125)147-84(66-60-54-48-42-35-29-23-17-11-5)74-96(127)151-106-98(115-92(123)73-83(65-59-53-47-41-34-28-22-16-10-4)146-93(124)67-61-55-49-43-36-30-24-18-12-6)107(143-79-89-101(130)105(150-95(126)72-82(119)64-58-52-46-40-33-27-21-15-9-3)97(108(148-89)157-159(138,139)140)114-91(122)71-81(118)63-57-51-45-39-32-26-20-14-8-2)149-90(104(106)156-158(135,136)137)80-144-111(109(131)132)76-87(100(129)102(153-111)86(121)77-116)152-112(110(133)134)75-85(120)99(128)103(154-112)88(78-117)155-160(141,142)145-70-69-113/h81-90,97-108,116-121,128-130H,7-80H2,1-6H3,(H,114,122)(H,115,123)(H,131,132)(H,133,134)(H,141,142)(H2,135,136,137)(H2,138,139,140)/q+1/p-7 FBBLZLDSYGPWQW-UHFFFAOYSA-G Extra-organism Membrane Periplasm logp 3.54 ALOGPS logs -4.79 ALOGPS solubility 4.07e-02 g/l ALOGPS logp 19.57 ChemAxon pka_strongest_acidic 0.57 ChemAxon iupac (2-{[1-(6-carboxylato-6-{[2-carboxylato-6-(1,2-dihydroxyethyl)-2-({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl}methoxy)-5-hydroxyoxan-4-yl]oxy}-3,4-dihydroxyoxan-2-yl)-2-hydroxyethyl phosphonato]oxy}ethyl)azaniumyl ChemAxon average_mass 2352.728 ChemAxon mono_mass 2351.277394933 ChemAxon smiles CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)C(OCC2OC(OP([O-])([O-])=O)C(NC(=O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)OC(COC2(CC(OC3(CC(O)C(O)C(O3)C(CO)OP([O-])(=O)OCC[N+])C([O-])=O)C(O)C(O2)C(O)CO)C([O-])=O)C1OP([O-])([O-])=O ChemAxon formula C112H199N3O42P3 ChemAxon inchi InChI=1S/C112H206N3O42P3/c1-7-13-19-25-31-37-38-44-50-56-62-68-94(125)147-84(66-60-54-48-42-35-29-23-17-11-5)74-96(127)151-106-98(115-92(123)73-83(65-59-53-47-41-34-28-22-16-10-4)146-93(124)67-61-55-49-43-36-30-24-18-12-6)107(143-79-89-101(130)105(150-95(126)72-82(119)64-58-52-46-40-33-27-21-15-9-3)97(108(148-89)157-159(138,139)140)114-91(122)71-81(118)63-57-51-45-39-32-26-20-14-8-2)149-90(104(106)156-158(135,136)137)80-144-111(109(131)132)76-87(100(129)102(153-111)86(121)77-116)152-112(110(133)134)75-85(120)99(128)103(154-112)88(78-117)155-160(141,142)145-70-69-113/h81-90,97-108,116-121,128-130H,7-80H2,1-6H3,(H,114,122)(H,115,123)(H,131,132)(H,133,134)(H,141,142)(H2,135,136,137)(H2,138,139,140)/q+1/p-7 ChemAxon inchikey FBBLZLDSYGPWQW-UHFFFAOYSA-G ChemAxon polar_surface_area 716.83 ChemAxon refractivity 601.44 ChemAxon polarizability 260.28 ChemAxon rotatable_bond_count 103 ChemAxon acceptor_count 34 ChemAxon donor_count 11 ChemAxon physiological_charge -6 ChemAxon formal_charge -6 ChemAxon Lipopolysaccharide biosynthesis E. 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. PW000831 ec00540 Metabolic lipopolysaccharide biosynthesis II E. 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 can either interact with a phosphoethanolamine resulting in a 1,2-diacyl-sn-glycerol and a phosphoethanolamine-Kdo2-lipid A which can be exported outside the cell, or it can interact 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. PW001905 Metabolic 46173153 26331809 60085 CPD-11653 Phosphoethanolamine transferase eptB P37661 EPTB_ECOLI eptB http://ecmdb.ca/proteins/P37661.xml Lipopolysaccharide export system permease protein lptG P0ADC6 LPTG_ECOLI lptG http://ecmdb.ca/proteins/P0ADC6.xml Lipopolysaccharide export system permease protein lptF P0AF98 LPTF_ECOLI lptF http://ecmdb.ca/proteins/P0AF98.xml Lipopolysaccharide export system ATP-binding protein lptB P0A9V1 LPTB_ECOLI lptB http://ecmdb.ca/proteins/P0A9V1.xml Lipopolysaccharide export system protein lptC P0ADV9 LPTC_ECOLI lptC http://ecmdb.ca/proteins/P0ADV9.xml Lipopolysaccharide export system protein lptA P0ADV1 LPTA_ECOLI lptA http://ecmdb.ca/proteins/P0ADV1.xml Lipopolysaccharide export system permease protein lptG P0ADC6 LPTG_ECOLI lptG http://ecmdb.ca/proteins/P0ADC6.xml Lipopolysaccharide export system permease protein lptF P0AF98 LPTF_ECOLI lptF http://ecmdb.ca/proteins/P0AF98.xml Adenosine triphosphate + Water + Phosphoethanolamine KDO(2)-lipid (A) > ADP + Hydrogen ion + Phosphate + Phosphoethanolamine KDO(2)-lipid (A) Adenosine triphosphate + Water + Phosphoethanolamine KDO(2)-lipid (A) > ADP + Hydrogen ion + Phosphate + Phosphoethanolamine KDO(2)-lipid (A) KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphoethanolamine KDO(2)-lipid (A) KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + Phosphoethanolamine KDO(2)-lipid (A) a-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 PE(16:0/16:0) + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > phosphoethanolamine-Kdo2-lipid A + 1,2-dihexadecanoyl-rac-glycerol + Phosphoethanolamine KDO(2)-lipid (A) PW_R005310