2.0 2012-05-31 14:50:41 -0600 2015-06-03 17:20:18 -0600 ECMDB20560 M2MDB001365 Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate or C5PP GlcNAc is involved in ECA biosynthesis. It is a substrate for Undecaprenyl-phosphate alpha-N-acetylglucosaminyl 1-phosphate transferase. This enzyme catalyzes the transfer of the GlcNAc-1-phosphate moiety from UDP-GlcNAc onto the carrier lipid undecaprenyl phosphate (C55-P), yielding GlcNAc-pyrophosphoryl-undecaprenyl (GlcNAc-PP-C55). It is the first lipid-linked intermediate involved in enterobacterial common antigen (ECA) synthesis and an acceptor for the addition of subsequent sugars to complete the biosynthesis of O-antigen (PMID 1730666). GlcNAc-pyrophosphorylundecaprenol functions as the acceptor of mannose residues for the in vivo synthesis of O8 side chains in E. coli.(PMID 7514591). Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae. 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. N-acetyl-D-glucosaminyldiphospho-undecaprenol N-acetyl-D-glucosaminyldiphosphoundecaprenol N-acetyl-glucosaminyl-pyrophosphorylundecaprenol N-[4,5-dihydroxy-2-[hydroxy-(hydroxy-(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaenoxy)phosphinoyl)oxy-phosphinoyl]oxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide C55-PP-GlcNAc Ditrans,polycis-undecaprenyl-N-acetyl-D-glucosaminyl diphosphate Ditrans,polycis-undecaprenyl-N-acetyl-D-glucosaminyl diphosphoric acid Glcnac-PP-lipid Glcnac-pyrophosphorylundecaprenol Lipid I N-Acetyl-D-glucosaminyldiphospho-undecaprenol N-Acetyl-D-glucosaminyldiphosphoundecaprenol N-Acetyl-glucosaminyl-pyrophosphorylundecaprenol N-[4,5-Dihydroxy-2-[hydroxy-(hydroxy-(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaenoxy)phosphinoyl)oxy-phosphinoyl]oxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide Prenyl-P-P-GlcNAc Undecaprenyl diphospho N-acetyl-glucosamine Undecaprenyl-N-acetyl-α-D-glucosaminyl-pyrophosphate Undecaprenyl-N-acetyl-D-glucosaminyl-pyrophosphate Undecaprenyl-n-acetyl-α-D-glucosaminyl-pyrophosphate Undecaprenyl-n-acetyl-α-D-glucosaminyl-pyrophosphoric acid Undecaprenyl-N-acetyl-a-D-glucosaminyl-pyrophosphate Undecaprenyl-N-acetyl-a-D-glucosaminyl-pyrophosphoric acid Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphoric acid Undecaprenyl-N-acetyl-D-glucosaminyl-pyrophosphate Undecaprenyl-n-acetyl-D-glucosaminyl-pyrophosphoric acid Undecaprenyl-N-acetyl-D-glucosaminyl-pyrophosphoric acid Undecaprenyl-N-acetyl-α-D-glucosaminyl-pyrophosphate Undecaprenyl-N-acetyl-α-D-glucosaminyl-pyrophosphoric acid C63H105NO12P2 1130.4548 1129.711200853 N-(4,5-dihydroxy-2-{[hydroxy({hydroxy[(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl)oxy]phosphoryl}oxy)phosphoryl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid N-[4,5-dihydroxy-2-({hydroxy[hydroxy(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl)oxyphosphoryl]oxyphosphoryl}oxy)-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(O)(=O)OP(O)(=O)OC1OC(CO)C(O)C(O)C1N=C(C)O InChI=1S/C63H105NO12P2/c1-47(2)24-14-25-48(3)26-15-27-49(4)28-16-29-50(5)30-17-31-51(6)32-18-33-52(7)34-19-35-53(8)36-20-37-54(9)38-21-39-55(10)40-22-41-56(11)42-23-43-57(12)44-45-73-77(69,70)76-78(71,72)75-63-60(64-58(13)66)62(68)61(67)59(46-65)74-63/h24,26,28,30,32,34,36,38,40,42,44,59-63,65,67-68H,14-23,25,27,29,31,33,35,37,39,41,43,45-46H2,1-13H3,(H,64,66)(H,69,70)(H,71,72) NEVJGTXBHJNFAZ-UHFFFAOYSA-N Membrane logp 8.48 ALOGPS logs -6.46 ALOGPS solubility 3.93e-04 g/l ALOGPS logp 14.82 ChemAxon pka_strongest_acidic 1.88 ChemAxon pka_strongest_basic 1.2 ChemAxon iupac N-(4,5-dihydroxy-2-{[hydroxy({hydroxy[(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl)oxy]phosphoryl}oxy)phosphoryl]oxy}-6-(hydroxymethyl)oxan-3-yl)ethanimidic acid ChemAxon average_mass 1130.4548 ChemAxon mono_mass 1129.711200853 ChemAxon smiles CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(O)(=O)OP(O)(=O)OC1OC(CO)C(O)C(O)C1N=C(C)O ChemAxon formula C63H105NO12P2 ChemAxon inchi InChI=1S/C63H105NO12P2/c1-47(2)24-14-25-48(3)26-15-27-49(4)28-16-29-50(5)30-17-31-51(6)32-18-33-52(7)34-19-35-53(8)36-20-37-54(9)38-21-39-55(10)40-22-41-56(11)42-23-43-57(12)44-45-73-77(69,70)76-78(71,72)75-63-60(64-58(13)66)62(68)61(67)59(46-65)74-63/h24,26,28,30,32,34,36,38,40,42,44,59-63,65,67-68H,14-23,25,27,29,31,33,35,37,39,41,43,45-46H2,1-13H3,(H,64,66)(H,69,70)(H,71,72) ChemAxon inchikey NEVJGTXBHJNFAZ-UHFFFAOYSA-N ChemAxon polar_surface_area 204.8 ChemAxon refractivity 330.92 ChemAxon polarizability 132.72 ChemAxon rotatable_bond_count 39 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Secondary Metabolites: enterobacterial common antigen biosynthesis 3 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. PW002046 Metabolic enterobacterial common antigen biosynthesis ECASYN-PWY Specdb::EiMs 2831 Specdb::MsMs 25376 Specdb::MsMs 25377 Specdb::MsMs 25378 Specdb::MsMs 31934 Specdb::MsMs 31935 Specdb::MsMs 31936 182 177 ACETYL-D-GLUCOSAMINYLDIPHOSPHO-UNDECAPRE Keseler, 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. 21097882 Rick, P. D., Mayer, H., Neumeyer, B. A., Wolski, S., Bitter-Suermann, D. (1985). "Biosynthesis of enterobacterial common antigen." J Bacteriol 162:494-503. 3886625 Rick, P. D., Hubbard, G. L., Barr, K. (1994). "Role of the rfe gene in the synthesis of the O8 antigen in Escherichia coli K-12." J Bacteriol 176:2877-2884. 7514591 Zheng, Y., Struck, D. K., Bernhardt, T. G., Young, R. (2008). "Genetic analysis of MraY inhibition by the phiX174 protein E." Genetics 180:1459-1466. 18791230 Undecaprenyl-phosphate alpha-N-acetylglucosaminyl 1-phosphate transferase P0AC78 WECA_ECOLI wecA http://ecmdb.ca/proteins/P0AC78.xml Probable UDP-N-acetyl-D-mannosaminuronic acid transferase P27836 WECG_ECOLI wecG http://ecmdb.ca/proteins/P27836.xml Uridine diphosphate-N-acetylglucosamine + Undecaprenyl phosphate > Uridine 5'-monophosphate + Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate UDP-N-Acetyl-D-mannosaminouronate + Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate > Hydrogen ion + Uridine 5'-diphosphate + Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate Di-trans,poly-cis-undecaprenyl phosphate + Uridine diphosphate-N-acetylglucosamine <> Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + Uridine 5'-monophosphate GLCNACPTRANS-RXN Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + UDP-N-Acetyl-D-mannosaminouronate <> Hydrogen ion + Undecaprenyl phosphate + Uridine 5'-diphosphate UDPMANACATRANS-RXN Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + UDP-ManNAcA > Uridine 5'-diphosphate + Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate + Hydrogen ion PW_R005973