2.0 2012-05-31 14:31:38 -0600 2015-06-03 17:19:28 -0600 ECMDB20178 M2MDB001025 N-Acetylmuramoyl-Ala N-acetylmuramoyl-Ala is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. 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. N-Acetyl-D-muramoyl-L-alanine C14H24N2O9 364.3484 364.148180376 (2R)-2-{[(2R)-2-{[(2S,3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene]amino}propanoic acid N-acetylmuramoyl-ala [H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(O)[C@]1([H])N=C(C)O)C(O)=N[C@]([H])(C)C(O)=O InChI=1S/C14H24N2O9/c1-5(13(21)22)15-12(20)6(2)24-11-9(16-7(3)18)14(23)25-8(4-17)10(11)19/h5-6,8-11,14,17,19,23H,4H2,1-3H3,(H,15,20)(H,16,18)(H,21,22)/t5-,6-,8-,9-,10-,11-,14+/m1/s1 ICMUIFDBEVJCQA-GQQBCVOHSA-N Cytoplasm Periplasm logp -1.27 ALOGPS logs -2.01 ALOGPS solubility 3.60e+00 g/l ALOGPS logp -1.4 ChemAxon pka_strongest_acidic 3.45 ChemAxon pka_strongest_basic 1.46 ChemAxon iupac (2R)-2-{[(2R)-2-{[(2S,3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene]amino}propanoic acid ChemAxon average_mass 364.3484 ChemAxon mono_mass 364.148180376 ChemAxon smiles [H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(O)[C@]1([H])N=C(C)O)C(O)=N[C@]([H])(C)C(O)=O ChemAxon formula C14H24N2O9 ChemAxon inchi InChI=1S/C14H24N2O9/c1-5(13(21)22)15-12(20)6(2)24-11-9(16-7(3)18)14(23)25-8(4-17)10(11)19/h5-6,8-11,14,17,19,23H,4H2,1-3H3,(H,15,20)(H,16,18)(H,21,22)/t5-,6-,8-,9-,10-,11-,14+/m1/s1 ChemAxon inchikey ICMUIFDBEVJCQA-GQQBCVOHSA-N ChemAxon polar_surface_area 181.63 ChemAxon refractivity 80.7 ChemAxon polarizability 34.93 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 11 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 33699 Specdb::CMs 48250 Specdb::CMs 136404 Specdb::CMs 144138 Specdb::NmrOneD 59312 Specdb::NmrOneD 59313 Specdb::NmrOneD 59314 Specdb::NmrOneD 59315 Specdb::NmrOneD 59316 Specdb::NmrOneD 59317 Specdb::NmrOneD 59318 Specdb::NmrOneD 59319 Specdb::NmrOneD 59320 Specdb::NmrOneD 59321 Specdb::NmrOneD 59322 Specdb::NmrOneD 59323 Specdb::NmrOneD 59324 Specdb::NmrOneD 59325 Specdb::NmrOneD 59326 Specdb::NmrOneD 59327 Specdb::NmrOneD 59328 Specdb::NmrOneD 59329 Specdb::NmrOneD 59330 Specdb::NmrOneD 59331 Specdb::MsMs 29498 Specdb::MsMs 29499 Specdb::MsMs 29500 Specdb::MsMs 36056 Specdb::MsMs 36057 Specdb::MsMs 36058 Specdb::MsMs 3225682 Specdb::MsMs 3225683 Specdb::MsMs 3225684 Specdb::MsMs 3225685 Specdb::MsMs 3225686 Specdb::MsMs 3225687 5462248 4575343 C02999 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 N-acetylmuramoyl-L-alanine amidase AmiB P26365 AMIB_ECOLI amiB http://ecmdb.ca/proteins/P26365.xml Probable N-acetylmuramoyl-L-alanine amidase AmiA P36548 AMIA_ECOLI amiA http://ecmdb.ca/proteins/P36548.xml N-acetylmuramoyl-L-alanine amidase AmiC P63883 AMIC_ECOLI amiC http://ecmdb.ca/proteins/P63883.xml N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine R04112 N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine N-Acetylmuramoyl-Ala + Water <> N-Acetyl-D-muramoate + L-Alanine