2.0 2012-05-31 14:53:51 -0600 2015-06-03 17:20:24 -0600 ECMDB20621 M2MDB001419 UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate-D-alanine UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate-D-alanine is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. It is a key component of peptidoglycan synthesis. The peptidoglycan synthesis pathway starts at the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . This final lipid intermediate is transferred through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks. UDP-N-acetylmuramoyl-L-alanyl-D-γ-Glu-6-carboxy-L-lys-D-ala UDP-N-acetylmuramoyl-L-alanyl-D-γ-glutamyl-6-carboxy-L-lysl-D-alaniine UDP-N-acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelyl-D-alanine UDP-Murnac-tetrapeptide UDP-n-Acetylmuramoyl-L-alanyl-D-γ-glu-6-carboxy-L-lys-D-ala UDP-n-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-6-carboxy-L-lysl-D-alaniine UDP-n-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-D-g-glu-6-carboxy-L-lys-D-ala UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-6-carboxy-L-lysl-D-alaniine UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-meso-2,6-diaminopimelyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-Glu-6-carboxy-L-lys-D-ala UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-6-carboxy-L-lysl-D-alaniine UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelyl-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioic acid-D-alanine UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glu-6-carboxy-L-lys-D-ala UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-6-carboxy-L-lysl-D-alaniine UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelyl-D-alanine Uridine 5'-pyrophosphoryl N-acetylmuramyl-tetrapeptide Uridine 5'-pyrophosphoryl N-acetylmuramyl-tetrapeptide C38H56N8O27P2 1118.8362 1118.27301165 1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5S,6R)-4-[(1R)-1-{[(1S)-1-{[(1R)-3-{[(1S,5R)-5-amino-5-carboxy-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}pentyl]carboximidato}-1-carboxypropyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}ethoxy]-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-2-yl phosphonato]oxy}phosphinato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-4-hydroxy-2-oxo-2,5-dihydro-1λ⁵-pyrimidine-1,5-bis(ylium) 1-[(2R,3R,4S,5R)-5-[({[(2R,3R,4R,5S,6R)-4-[(1R)-1-{[(1S)-1-{[(1R)-3-{[(1S,5R)-5-amino-5-carboxy-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}pentyl]carboximidato}-1-carboxypropyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}ethoxy]-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-2-yl phosphonato]oxyphosphinato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-4-hydroxy-2-oxo-5H-1λ⁵-pyrimidine-1,5-bis(ylium) [H][C@@](N)(CCC[C@]([H])(N=C([O-])CC[C@@]([H])(N=C(O)[C@]([H])(C)N=C(O)[C@@]([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP([O-])(=O)OP([O-])(=O)OC[C@@]2([H])O[C@@]([H])([N+]3=C[CH+]C(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)[O-])C(O)=O)C(O)=N[C@]([H])(C)C(O)=O)C(O)=O InChI=1S/C38H58N8O27P2/c1-14(30(54)44-20(36(61)62)8-9-23(49)43-19(7-5-6-18(39)35(59)60)32(56)41-15(2)34(57)58)40-31(55)16(3)69-29-25(42-17(4)48)37(71-21(12-47)27(29)52)72-75(66,67)73-74(64,65)68-13-22-26(51)28(53)33(70-22)46-11-10-24(50)45-38(46)63/h10-11,14-16,18-22,25-29,33,37,47,51-53H,5-9,12-13,39H2,1-4H3,(H9-2,40,41,42,43,44,45,48,49,50,54,55,56,57,58,59,60,61,62,63,64,65,66,67)/p-2/t14-,15+,16+,18+,19-,20+,21+,22+,25+,26+,27+,28+,29+,33+,37+/m0/s1 UHRGSQREVOYTOH-HOZNVNQUSA-L Cytoplasm Periplasm logp 0.67 ALOGPS logs -3.35 ALOGPS solubility 5.60e-01 g/l ALOGPS logp -6.1 ChemAxon pka_strongest_acidic -6.9 ChemAxon iupac 1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5S,6R)-4-[(1R)-1-{[(1S)-1-{[(1R)-3-{[(1S,5R)-5-amino-5-carboxy-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}pentyl]carboximidato}-1-carboxypropyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}ethoxy]-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-2-yl phosphonato]oxy}phosphinato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-4-hydroxy-2-oxo-2,5-dihydro-1λ⁵-pyrimidine-1,5-bis(ylium) ChemAxon average_mass 1118.8362 ChemAxon mono_mass 1118.27301165 ChemAxon smiles [H][C@@](N)(CCC[C@]([H])(N=C([O-])CC[C@@]([H])(N=C(O)[C@]([H])(C)N=C(O)[C@@]([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP([O-])(=O)OP([O-])(=O)OC[C@@]2([H])O[C@@]([H])([N+]3=C[CH+]C(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)[O-])C(O)=O)C(O)=N[C@]([H])(C)C(O)=O)C(O)=O ChemAxon formula C38H56N8O27P2 ChemAxon inchi InChI=1S/C38H58N8O27P2/c1-14(30(54)44-20(36(61)62)8-9-23(49)43-19(7-5-6-18(39)35(59)60)32(56)41-15(2)34(57)58)40-31(55)16(3)69-29-25(42-17(4)48)37(71-21(12-47)27(29)52)72-75(66,67)73-74(64,65)68-13-22-26(51)28(53)33(70-22)46-11-10-24(50)45-38(46)63/h10-11,14-16,18-22,25-29,33,37,47,51-53H,5-9,12-13,39H2,1-4H3,(H9-2,40,41,42,43,44,45,48,49,50,54,55,56,57,58,59,60,61,62,63,64,65,66,67)/p-2/t14-,15+,16+,18+,19-,20+,21+,22+,25+,26+,27+,28+,29+,33+,37+/m0/s1 ChemAxon inchikey UHRGSQREVOYTOH-HOZNVNQUSA-L ChemAxon polar_surface_area 575.76 ChemAxon refractivity 256.48 ChemAxon polarizability 101.01 ChemAxon rotatable_bond_count 29 ChemAxon acceptor_count 31 ChemAxon donor_count 12 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Specdb::NmrOneD 258248 Specdb::NmrOneD 258249 Specdb::NmrOneD 258250 Specdb::NmrOneD 258251 Specdb::NmrOneD 258252 Specdb::NmrOneD 258253 Specdb::NmrOneD 258254 Specdb::NmrOneD 258255 Specdb::NmrOneD 258256 Specdb::NmrOneD 258257 Specdb::NmrOneD 258258 Specdb::NmrOneD 258259 Specdb::NmrOneD 258260 Specdb::NmrOneD 258261 Specdb::NmrOneD 258262 Specdb::NmrOneD 258263 Specdb::NmrOneD 258264 Specdb::NmrOneD 258265 Specdb::NmrOneD 258266 Specdb::NmrOneD 258267 Specdb::MsMs 29618 Specdb::MsMs 29619 Specdb::MsMs 29620 Specdb::MsMs 36176 Specdb::MsMs 36177 Specdb::MsMs 36178 25200511 UDP-MURNAC-TETRAPEPTIDE 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Murein tetrapeptide carboxypeptidase P76008 LDCA_ECOLI ldcA http://ecmdb.ca/proteins/P76008.xml UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate-D-alanine + Water > L-Alanine + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate RXN0-2061