2.0 2012-05-31 14:07:15 -0600 2015-06-03 15:54:49 -0600 ECMDB04170 M2MDB000650 UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate UDP-n-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate 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-γ-D-glutamyl-meso-diaminopimelate UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate UDP-Aagm-diaminoheptanedioate UDP-Aagm-diaminoheptanedioic acid UDP-MurNAc-L-Ala-D-Glu-meso-A2pm UDP-MurNAc-L-Ala-D-Glu-meso-A2pm UDP-MurNAc-L-Ala-D-Glu-mesoA2pm UDP-n-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelate UDP-n-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelic acid UDP-N-acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-meso-2,6-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-meso-2,6-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioic acid UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-g-D-glutamyl-meso-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-g-D-glutamyl-meso-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-meso-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelic acid C35H51N7O26P2 1047.7583 1047.235897863 (4R)-N-[(1S,5R)-5-amino-1,5-dicarboxypentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-oxidopropylidene]amino}butanecarboximidate (4R)-N-[(1S,5R)-5-amino-1,5-dicarboxypentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-oxidopropylidene]amino}butanecarboximidate [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])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)[O-])C(O)=O)C(O)=O)C(O)=O InChI=1S/C35H55N7O26P2/c1-13(28(50)40-18(33(56)57)7-8-21(45)39-17(32(54)55)6-4-5-16(36)31(52)53)37-29(51)14(2)64-27-23(38-15(3)44)34(66-19(11-43)25(27)48)67-70(61,62)68-69(59,60)63-12-20-24(47)26(49)30(65-20)42-10-9-22(46)41-35(42)58/h9-10,13-14,16-20,23-27,30,34,43,47-49H,4-8,11-12,36H2,1-3H3,(H,37,51)(H,38,44)(H,39,45)(H,40,50)(H,52,53)(H,54,55)(H,56,57)(H,59,60)(H,61,62)(H,41,46,58)/p-4/t13-,14+,16+,17-,18+,19+,20+,23+,24+,25+,26+,27+,30+,34+/m0/s1 QUHLBZKCGUXHGP-BHBBPGSKSA-J Cytosol logp -0.82 ALOGPS logs -2.45 ALOGPS solubility 4.00e+00 g/l ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 1.72 ChemAxon iupac (4R)-N-[(1S,5R)-5-amino-1,5-dicarboxypentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-oxidopropylidene]amino}butanecarboximidate ChemAxon average_mass 1047.7583 ChemAxon mono_mass 1047.235897863 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])(N3C=CC([O-])=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)[O-])C(O)=O)C(O)=O)C(O)=O ChemAxon formula C35H51N7O26P2 ChemAxon inchi InChI=1S/C35H55N7O26P2/c1-13(28(50)40-18(33(56)57)7-8-21(45)39-17(32(54)55)6-4-5-16(36)31(52)53)37-29(51)14(2)64-27-23(38-15(3)44)34(66-19(11-43)25(27)48)67-70(61,62)68-69(59,60)63-12-20-24(47)26(49)30(65-20)42-10-9-22(46)41-35(42)58/h9-10,13-14,16-20,23-27,30,34,43,47-49H,4-8,11-12,36H2,1-3H3,(H,37,51)(H,38,44)(H,39,45)(H,40,50)(H,52,53)(H,54,55)(H,56,57)(H,59,60)(H,61,62)(H,41,46,58)/p-4/t13-,14+,16+,17-,18+,19+,20+,23+,24+,25+,26+,27+,30+,34+/m0/s1 ChemAxon inchikey QUHLBZKCGUXHGP-BHBBPGSKSA-J ChemAxon polar_surface_area 543.4 ChemAxon refractivity 263.32 ChemAxon polarizability 92.98 ChemAxon rotatable_bond_count 27 ChemAxon acceptor_count 29 ChemAxon donor_count 11 ChemAxon physiological_charge -3 ChemAxon formal_charge -4 ChemAxon Lysine biosynthesis Lysine is biosynthesized from L-aspartic acid. L-aspartic acid can be incorporated into the cell through various methods: C4 dicarboxylate / orotate:H+ symporter , glutamate / aspartate : H+ symporter GltP, dicarboxylate transporter , C4 dicarboxylate / C4 monocarboxylate transporter DauA, glutamate / aspartate ABC transporter L-aspartic acid is phosphorylated by an ATP-driven Aspartate kinase resulting in ADP and L-aspartyl-4-phosphate. L-aspartyl-4-phosphate is then dehydrogenated through an NADPH driven aspartate semialdehyde dehydrogenase resulting in a release of phosphate, NADP and L-aspartic 4-semialdehyde (involved in methionine biosynthesis). L-aspartic 4-semialdehyde interacts with a pyruvic acid through a 4-hydroxy-tetrahydrodipicolinate synthase resulting in a release of hydrogen ion, water and (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate. The latter compound is then reduced by an NADPH driven 4-hydroxy-tetrahydrodipicolinate reductase resulting in a release of water, NADP and (S)-2,3,4,5-tetrahydrodipicolinate, This compound interacts with succinyl-CoA and water through a tetrahydrodipicolinate succinylase resulting in a release of coenzyme A and N-Succinyl-2-amino-6-ketopimelate. This compound interacts with L-glutamic acid through a N-succinyldiaminopimelate aminotransferase resulting in oxoglutaric acid, N-succinyl-L,L-2,6-diaminopimelate. The latter compound is then desuccinylated by reacting with water through a N-succinyl-L-diaminopimelate desuccinylase resulting in a succinic acid and L,L-diaminopimelate. This compound is then isomerized through a diaminopimelate epimerase resulting in a meso-diaminopimelate (involved in peptidoglyccan biosynthesis I). This compound is then decarboxylated by a diaminopimelate decarboxylase resulting in a release of carbon dioxide and L-lysine. L-lysine is then incorporated into lysine degradation pathway. Lysine also regulate its own biosynthesis by repressing dihydrodipicolinate synthase and also repressing lysine-sensitive aspartokinase 3. A metabolic connection joins synthesis of an amino acid, lysine, to synthesis of cell wall material. Diaminopimelate is a precursor both for lysine and for cell wall components. The synthesis of lysine, methionine and threonine share two reactions at the start of the three pathways, the reactions converting L-aspartate to L-aspartate semialdehyde. The reaction involving aspartate kinase is carried out by three isozymes, one specific for synthesis of each end product amino acid. Each of the three aspartate kinase isozymes is regulated by its corresponding end product amino acid. PW000771 ec00300 Metabolic Peptidoglycan biosynthesis ec00550 UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing) PWY-6387 Specdb::NmrOneD 286735 Specdb::NmrOneD 286736 Specdb::NmrOneD 286737 Specdb::NmrOneD 286738 Specdb::NmrOneD 286739 Specdb::NmrOneD 286740 Specdb::NmrOneD 286741 Specdb::NmrOneD 286742 Specdb::NmrOneD 286743 Specdb::NmrOneD 286744 Specdb::NmrOneD 286745 Specdb::NmrOneD 286746 Specdb::NmrOneD 286747 Specdb::NmrOneD 286748 Specdb::NmrOneD 286749 Specdb::NmrOneD 286750 Specdb::NmrOneD 286751 Specdb::NmrOneD 286752 Specdb::NmrOneD 286753 Specdb::NmrOneD 286754 Specdb::MsMs 24644 Specdb::MsMs 24645 Specdb::MsMs 24646 Specdb::MsMs 31202 Specdb::MsMs 31203 Specdb::MsMs 31204 25243985 C04877 28639 UDP-AAGM-DIAMINOHEPTANEDIOATE 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 Kanehisa, 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. 22080510 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 UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase P11880 MURF_ECOLI murF http://ecmdb.ca/proteins/P11880.xml UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligase P22188 MURE_ECOLI murE http://ecmdb.ca/proteins/P22188.xml Murein tetrapeptide carboxypeptidase P76008 LDCA_ECOLI ldcA http://ecmdb.ca/proteins/P76008.xml UDP-N-acetylmuramate:L-alanyl-gamma-D-glutamyl-meso-diaminopimelate ligase P37773 MPL_ECOLI mpl http://ecmdb.ca/proteins/P37773.xml Diaminopimelic acid + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine R04617 UDP-NACMURALGLDAPAALIG-RXN Water + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate-D-alanine > D-Alanine + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + Adenosine triphosphate + UDP-N-Acetylmuraminate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Meso-2,6-Diaminoheptanedioate <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate R02788 Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + D-Alanyl-D-alanine <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine R04617 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 UDP-N-Acetylmuraminate + L-Ala-D-Glu-meso-A2pm + Adenosine triphosphate > Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP + Phosphate RXN0-2361 meso-diaminopimelate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Adenosine triphosphate > Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + Phosphate + ADP UDP-NACMURALGLDAPLIG-RXN D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Meso-2,6-Diaminoheptanedioate <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Meso-2,6-Diaminoheptanedioate <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate