2.02012-07-30 14:54:39 -06002015-06-03 17:20:39 -0600ECMDB21112M2MDB0015211,6-Anhydrous-N-Acetylmuramyl-tripeptide1,6-anhydrous-n-acetylmuramyl-tripeptide belongs to the class of 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. (inferred from compound structure)C26H43N5O14649.6447649.280651109(6S)-2-amino-6-{[(2R)-4-carboxy-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5S)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}heptanedioic acid(6S)-2-amino-6-{[(2R)-4-carboxy-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5S)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}heptanedioic acid[H]C(N)(CCC[C@]([H])(N=C(O)[C@@]([H])(CCC(O)=O)N=C(O)[C@]([H])(C)N=C(O)[C@@]([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC[C@]1([H])N=C(C)O)C(O)=O)C(O)=OInChI=1S/C26H43N5O14/c1-11(28-23(38)12(2)45-21-17(29-13(3)33)10-44-18(9-32)20(21)36)22(37)30-15(7-8-19(34)35)24(39)31-16(26(42)43)6-4-5-14(27)25(40)41/h11-12,14-18,20-21,32,36H,4-10,27H2,1-3H3,(H,28,38)(H,29,33)(H,30,37)(H,31,39)(H,34,35)(H,40,41)(H,42,43)/t11-,12+,14?,15+,16-,17-,18+,20+,21+/m0/s1KGVLFEPQSVUIRC-FYQNUYSYSA-NCytosollogp-1.80logs-3.71solubility1.26e-01 g/llogp-3.7pka_strongest_acidic1.71pka_strongest_basic9.53iupac(6S)-2-amino-6-{[(2R)-4-carboxy-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5S)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}heptanedioic acidaverage_mass649.6447mono_mass649.280651109smiles[H]C(N)(CCC[C@]([H])(N=C(O)[C@@]([H])(CCC(O)=O)N=C(O)[C@]([H])(C)N=C(O)[C@@]([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC[C@]1([H])N=C(C)O)C(O)=O)C(O)=OformulaC26H43N5O14inchiInChI=1S/C26H43N5O14/c1-11(28-23(38)12(2)45-21-17(29-13(3)33)10-44-18(9-32)20(21)36)22(37)30-15(7-8-19(34)35)24(39)31-16(26(42)43)6-4-5-14(27)25(40)41/h11-12,14-18,20-21,32,36H,4-10,27H2,1-3H3,(H,28,38)(H,29,33)(H,30,37)(H,31,39)(H,34,35)(H,40,41)(H,42,43)/t11-,12+,14?,15+,16-,17-,18+,20+,21+/m0/s1inchikeyKGVLFEPQSVUIRC-FYQNUYSYSA-Npolar_surface_area327.2refractivity149.24polarizability63.89rotatable_bond_count19acceptor_count19donor_count10physiological_charge-1formal_charge0D-Alanine metabolismL-alanine is an essential component of protein and peptidoglycan. The latter also contains about three molecules of D-alanine for every L-alanine. Only about 10 percent of the total alanine synthesized flows into peptidoglycan.
Refer to L-alanine metabolism (pathway PW000788 ).
Through this single pathway D-alanine can be degraded to pyruvate through a D-amino acid dehydrogenase, which enters central metabolism and thereby can serve as a total source of carbon and energy. This pathway is unique among those through which L-amino acids are degraded, in that the L form must first be converted to the D form. This first step of the pathway, which can be catalyzed by either of two racemases( biosynthetic or catabolic), also serves an essential role in biosynthesis because its product, D-alanine, is an essential component of cell wall peptidoglycan (murein). D-alanine is metabolized by an ATP driven D-alanine ligase A and B resulting in D-alanyl-D-alanine. This product is incorporated into the peptidoglycan biosynthesis.
PW000768ec00473MetabolicSpecdb::CMs1083648Specdb::EiMs4412Specdb::NmrOneD289955Specdb::NmrOneD289956Specdb::NmrOneD289957Specdb::NmrOneD289958Specdb::NmrOneD289959Specdb::NmrOneD289960Specdb::NmrOneD289961Specdb::NmrOneD289962Specdb::NmrOneD289963Specdb::NmrOneD289964Specdb::NmrOneD289965Specdb::NmrOneD289966Specdb::NmrOneD289967Specdb::NmrOneD289968Specdb::NmrOneD289969Specdb::NmrOneD289970Specdb::NmrOneD289971Specdb::NmrOneD289972Specdb::NmrOneD289973Specdb::NmrOneD289974Specdb::MsMs25865Specdb::MsMs25866Specdb::MsMs25867Specdb::MsMs32423Specdb::MsMs32424Specdb::MsMs3242546173119CPD0-2284Beta-hexosaminidaseP75949NAGZ_ECOLInagZhttp://ecmdb.ca/proteins/P75949.xmlMurein tetrapeptide carboxypeptidaseP76008LDCA_ECOLIldcAhttp://ecmdb.ca/proteins/P76008.xml1,6-anhydro-N-acetylmuramyl-L-alanine amidase AmpDP13016AMPD_ECOLIampDhttp://ecmdb.ca/proteins/P13016.xml1,6-Anhydrous-N-Acetylmuramyl-tripeptide + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + 1,6-Anhydro-N-acetylmuramateN-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptide1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptide