2.02012-10-10 12:20:52 -06002015-06-03 17:26:06 -0600ECMDB23181M2MDB003571TDP-Fuc4NAcTDP-Fuc4NAc is an intermediate in LPS biosynthesis. It is a substrate for 4-alpha-L-fucosyltransferase which catalyzes the reaction TDP-Fuc4NAc + Und-PP-GlcNAc-ManNAcA = TDP + Und-PP-GlcNAc-ManNAcA-Fuc4NAc. It is part of the reaction that synthesizes lipid III, the third lipid-linked intermediate in enterobacterial common antigen (ECA) or LPS biosynthesis.C18H29N3O15P2589.3815589.107390297[({[(2R,3R,4S,5R,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid{[(2R,3R,4S,5R,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy(hydroxy)phosphoryl}oxy[3-hydroxy-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methoxyphosphinic acid[H]OC1([H])C([H])([H])C([H])(OC1([H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])O[C@@]1([H])O[C@]([H])(C([H])([H])[H])[C@]([H])(N([H])C(=O)C([H])([H])[H])[C@]([H])(O[H])[C@@]1([H])O[H])N1C([H])=C(C(=O)N([H])C1=O)C([H])([H])[H]InChI=1S/C18H29N3O15P2/c1-7-5-21(18(27)20-16(7)26)12-4-10(23)11(34-12)6-32-37(28,29)36-38(30,31)35-17-15(25)14(24)13(8(2)33-17)19-9(3)22/h5,8,10-15,17,23-25H,4,6H2,1-3H3,(H,19,22)(H,28,29)(H,30,31)(H,20,26,27)/t8-,10?,11?,12?,13+,14+,15-,17-/m1/s1YHXQWYBLXUELDA-QVDZPGAXSA-Nlogp-0.98logs-1.93solubility7.00e+00 g/llogp-2.9pka_strongest_acidic1.74pka_strongest_basic-0.38iupac[({[(2R,3R,4S,5R,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acidaverage_mass589.3815mono_mass589.107390297smiles[H]OC1([H])C([H])([H])C([H])(OC1([H])C([H])([H])OP(=O)(O[H])OP(=O)(O[H])O[C@@]1([H])O[C@]([H])(C([H])([H])[H])[C@]([H])(N([H])C(=O)C([H])([H])[H])[C@]([H])(O[H])[C@@]1([H])O[H])N1C([H])=C(C(=O)N([H])C1=O)C([H])([H])[H]formulaC18H29N3O15P2inchiInChI=1S/C18H29N3O15P2/c1-7-5-21(18(27)20-16(7)26)12-4-10(23)11(34-12)6-32-37(28,29)36-38(30,31)35-17-15(25)14(24)13(8(2)33-17)19-9(3)22/h5,8,10-15,17,23-25H,4,6H2,1-3H3,(H,19,22)(H,28,29)(H,30,31)(H,20,26,27)/t8-,10?,11?,12?,13+,14+,15-,17-/m1/s1inchikeyYHXQWYBLXUELDA-QVDZPGAXSA-Npolar_surface_area259.95refractivity118.86polarizability50.35rotatable_bond_count9acceptor_count12donor_count7physiological_charge-2formal_charge0Secondary Metabolites: enterobacterial common antigen biosynthesis
The biosynthesis of a enterobacterial common antigen can begin with a di-trans,octa-cis-undecaprenyl phosphate interacts with a Uridine diphosphate-N-acetylglucosamine through undecaprenyl-phosphate α-N-acetylglucosaminyl transferase resulting in a N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol and a Uridine 5'-monophosphate. The N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol then reacts with an UDP-ManNAcA from the Amino sugar and nucleotide sugar metabolism pathway. This reaction is metabolized by a UDP-N-acetyl-D-mannosaminuronic acid transferase resulting in a uridine 5' diphosphate, a hydrogen ion and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate.
Glucose 1 phosphate can be metabolize by interacting with a hydrogen ion and a thymidine 5-triphosphate by either reacting with a dTDP-glucose pyrophosphorylase or a dTDP-glucose pyrophosphorylase 2 resulting in the release of a pyrophosphate and a dTDP-D-glucose. The latter compound is then dehydrated through an dTDP-glucose 4,6-dehydratase 2 resulting in water and dTDP-4-dehydro-6-deoxy-D-glucose. The latter compound interacts with L-glutamic acid through a dTDP-4-dehydro-6-deoxy-D-glucose transaminase resulting in the release of oxoglutaric acid and dTDP-thomosamine. The latter compound interacts with acetyl-coa through a dTDP-fucosamine acetyltransferase resulting in a Coenzyme A, a hydrogen Ion and a TDP-Fuc4NAc.
Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate then interacts with a TDP--Fuc4NAc through a 4-acetamido-4,6-dideoxy-D-galactose transferase resulting in a hydrogen ion, a dTDP and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. This compound is then transported through a protein wzxE into the periplasmic space so that it can be incorporated into the outer membrane
Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae. ECA is a unique cell surface antigen that can be found in the outer leaflet of the outer membrane. The carbohydrate portion consists of N-acetyl-glucosamine, N-acetyl-D-mannosaminuronic acid and 4-acetamido-4,6-dideoxy-D-galactose. These amino sugars form trisaccharide repeat units which are part of linear heteropolysaccharide chains.PW000959MetabolicSecondary Metabolites: enterobacterial common antigen biosynthesis 2The biosynthesis of a enterobacterial common antigen can begin with a di-trans,octa-cis-undecaprenyl phosphate interacts with a Uridine diphosphate-N-acetylglucosamine through undecaprenyl-phosphate α-N-acetylglucosaminyl transferase resulting in a N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol and a Uridine 5'-monophosphate. The N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol then reacts with an UDP-ManNAcA from the Amino sugar and nucleotide sugar metabolism pathway. This reaction is metabolized by a UDP-N-acetyl-D-mannosaminuronic acid transferase resulting in a uridine 5' diphosphate, a hydrogen ion and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. Glucose 1 phosphate can be metabolize by interacting with a hydrogen ion and a thymidine 5-triphosphate by either reacting with a dTDP-glucose pyrophosphorylase or a dTDP-glucose pyrophosphorylase 2 resulting in the release of a pyrophosphate and a dTDP-D-glucose. The latter compound is then dehydrated through an dTDP-glucose 4,6-dehydratase 2 resulting in water and dTDP-4-dehydro-6-deoxy-D-glucose. The latter compound interacts with L-glutamic acid through a dTDP-4-dehydro-6-deoxy-D-glucose transaminase resulting in the release of oxoglutaric acid and dTDP-thomosamine. The latter compound interacts with acetyl-coa through a dTDP-fucosamine acetyltransferase resulting in a Coenzyme A, a hydrogen Ion and a TDP-Fuc4NAc. Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate then interacts with a TDP--Fuc4NAc through a 4-acetamido-4,6-dideoxy-D-galactose transferase resulting in a hydrogen ion, a dTDP and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. This compound is then transported through a protein wzxE into the periplasmic space so that it can be incorporated into the outer membrane Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae. ECA is a unique cell surface antigen that can be found in the outer leaflet of the outer membrane. The carbohydrate portion consists of N-acetyl-glucosamine, N-acetyl-D-mannosaminuronic acid and 4-acetamido-4,6-dideoxy-D-galactose. These amino sugars form trisaccharide repeat units which are part of linear heteropolysaccharide chains.PW002045MetabolicSpecdb::CMs1083502Specdb::NmrOneD332938Specdb::NmrOneD332939Specdb::NmrOneD332940Specdb::NmrOneD332941Specdb::NmrOneD332942Specdb::NmrOneD332943Specdb::NmrOneD332944Specdb::NmrOneD332945Specdb::NmrOneD332946Specdb::NmrOneD332947Specdb::NmrOneD332948Specdb::NmrOneD332949Specdb::NmrOneD332950Specdb::NmrOneD332951Specdb::NmrOneD332952Specdb::NmrOneD332953Specdb::NmrOneD332954Specdb::NmrOneD332955Specdb::NmrOneD332956Specdb::NmrOneD332957Specdb::MsMs29114Specdb::MsMs29115Specdb::MsMs29116Specdb::MsMs35672Specdb::MsMs35673Specdb::MsMs356744-alpha-L-fucosyltransferaseP56258WECF_ECOLIwecFhttp://ecmdb.ca/proteins/P56258.xmlLipopolysaccharide biosynthesis protein rffCP27832RFFC_ECOLIrffChttp://ecmdb.ca/proteins/P27832.xmlTDP-Fuc4NAc + Und-PP-GlcNAc-ManNAcA > Thiamine pyrophosphate + Und-PP-GlcNAc-ManNAcA-Fuc4NAcUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate + TDP-Fuc4NAc + Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate > Hydrogen ion + dTDP + Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate + Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactosePW_R003702Acetyl-CoA + dTDP-thomosamine > TDP-Fuc4NAc + Coenzyme A + Hydrogen ionPW_R003703