2.02012-05-31 13:49:38 -06002015-09-13 12:56:10 -0600ECMDB01310M2MDB000333D-AlanineD-Alanine is an amino acid and one of the most important molecules in living organisms. It has a chiral carbon at a -position.(R)-AlanineD(-)-a -AlanineD(-)-a-AlanineD(-)-alpha-AlanineD(-)-α-AlanineD-(-)-AlanineD-2-AminopropionateD-2-Aminopropionic acidD-a-AlanineD-AlaD-AlanineD-alpha-AlanineD-α-AlanineDelta-(-)-AlanineDelta-2-AminopropionateDelta-2-Aminopropionic aciddelta-a-AlanineDelta-AlanineDelta-alpha-AlanineDl-Alanineδ-(-)-Alanineδ-2-Aminopropionateδ-2-Aminopropionic acidδ-a-Alanineδ-Alanineδ-α-AlanineC3H7NO289.093289.047678473(2R)-2-aminopropanoic acidD-alanine338-69-2C[C@@H](N)C(O)=OInChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1QNAYBMKLOCPYGJ-UWTATZPHSA-NSolidCytosolExtra-organismPeriplasmlogp-3.05logs0.70solubility4.47e+02 g/lmelting_point292 oClogp-2.8pka_strongest_acidic2.47pka_strongest_basic9.48iupac(2R)-2-aminopropanoic acidaverage_mass89.0932mono_mass89.047678473smilesC[C@@H](N)C(O)=OformulaC3H7NO2inchiInChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1inchikeyQNAYBMKLOCPYGJ-UWTATZPHSA-Npolar_surface_area63.32refractivity20.5polarizability8.54rotatable_bond_count1acceptor_count3donor_count2physiological_charge0formal_charge0Vitamin B6 metabolismec00750Peptidoglycan biosynthesisec00550D-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.
PW000768ec00473MetabolicMetabolic pathwayseco01100Vancomycin resistanceeco01502L-alanine metabolismL-alanine is an essential component of proteins 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.
There are at least 3 ways to begin the biosynthesis of alanine.
The first method for alanine biosynthesis begins with L-cysteine produced from L-cysteine biosynthesis pathway. L-cysteine reacts with an [L-cysteine desulfurase] L-cysteine persulfide through a cysteine desulfurase resulting in a release of [L-cysteine desulfurase] l-cysteine persulfide and L-alanine.
The second method starts with pyruvic acid reacting with L-glutamic acid through a glutamate-pyruvate aminotransferase resulting in a oxoglutaric acid and L-alanine.
The third method starts with L-glutamic acid interacting with Alpha-ketoisovaleric acid through a valine transaminase resulting in an oxoglutaric acid and L-valine. L-valine reacts with pyruvic acid through a valine-pyruvate aminotransferase resulting Alpha-ketoisovaleric acid and L-alanine.
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.
L-alanine is metabolized with alanine racemase, either catabolic or metabolic resulting in a D-alanine. This compound reacts with water and a quinone through a
D-amino acid dehydrogenase resulting in Pyruvic acid, hydroquinone and ammonium, thus entering the 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.
D-alanine, is an essential component of cell wall peptidoglycan (murein). The role of the alr racemase is predominately biosynthetic: it is produced constitutively in small amounts. The role of the dadX racemase is degradative: it is induced to high levels by alanine and is subject to catabolite repression.
PW000788Metabolicinner membrane transportlist of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol
This pathway should be updated regularly with the new inner membrae transports addedPW000786Metabolicpeptidoglycan biosynthesis IPeptidoglycan is a net-like polymer which surrounds the cytoplasmic membrane of most bacteria and functions to maintain cell shape and prevent rupture due to the internal turgor.In E. coli K-12, the peptidoglycan consists of glycan strands of alternating subunits of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) which are cross-linked by short peptides. The pathway for constructing this net involves two cell compartments: cytoplasm and periplasmic space.
The pathway starts with a beta-D-fructofuranose going through a mannose PTS permease, phosphorylating the compund and producing a beta-D-fructofuranose 6 phosphate. This compound can be obtained from the glycolysis and pyruvate dehydrogenase or from an isomerization reaction of Beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase.The compound Beta-D-fructofuranose 6 phosphate and L-Glutamine react with a glucosamine fructose-6-phosphate aminotransferase, thus producing a glucosamine 6-phosphate and a l-glutamic acid. The glucosamine 6-phosphate interacts with phosphoglucosamine mutase in a reversible reaction producing glucosamine-1P. Glucosamine-1p and acetyl coa undergo acetylation throuhg a bifunctional protein glmU releasing Coa and a hydrogen ion and producing a N-acetyl-glucosamine 1-phosphate. Glmu, being a bifunctional protein, follows catalyze the interaction of N-acetyl-glucosamine 1-phosphate, hydrogen ion and UTP into UDP-N-acetylglucosamine and pyrophosphate. UDP-N-acetylglucosamine then interacts with phosphoenolpyruvic acid and a UDP-N acetylglucosamine 1- carboxyvinyltransferase realeasing a phosphate and the compound UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate. This compound undergoes a NADPH dependent reduction producing a UDP-N-acetyl-alpha-D-muramate through a UDP-N-acetylenolpyruvoylglucosamine reductase. UDP-N-acetyl-alpha-D-muramate and L-alanine react in an ATP-mediated ligation through a UDP-N-acetylmuramate-alanine ligase releasing an ADP, hydrogen ion, a phosphate and a UDP-N-acetylmuramoyl-L-alanine. This compound interacts with D-glutamic acid and ATP through UDP-N-acetylmuramoylalanine-D-glutamate ligase releasing ADP, A phosphate and UDP-N-acetylmuramoyl-L-alanyl-D-glutamate. The latter compound then interacts with meso-diaminopimelate in an ATP mediated ligation through a UDP-N-acetylmuramoylalanine-D-glutamate-2,6-diaminopimelate ligase resulting in ADP, phosphate, hydrogen ion and UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate. This compound in turn with D-alanyl-D-alanine react in an ATP-mediated ligation through UDP-N-Acetylmuramoyl-tripeptide-D-alanyl-D-alanine ligase to produce UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine and hydrogen ion, ADP, phosphate. UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine interacts with di-trans,octa-cis-undecaprenyl phosphate through a phospho-N-acetylmuramoyl-pentapeptide-transferase, resulting in UMP and Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine which in turn reacts with a UDP-N-acetylglucosamine through a N-acetylglucosaminyl transferase to produce a hydrogen, UDP and ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-gamma-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine. This compound ends the cytoplasmic part of the pathway. ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-gamma-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine is transported through a lipi II flippase. Once in the periplasmic space, the compound reacts with a penicillin binding protein 1A prodducing a peptidoglycan dimer, a hydrogen ion, and UDP. The peptidoglycan dimer then reacts with a penicillin binding protein 1B producing a peptidoglycan with D,D, cross-links and a D-alanine.
PW000906Metabolicpeptidoglycan biosynthesis I 2Peptidoglycan is a net-like polymer which surrounds the cytoplasmic membrane of most bacteria and functions to maintain cell shape and prevent rupture due to the internal turgor.In E. coli K-12, the peptidoglycan consists of glycan strands of alternating subunits of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) which are cross-linked by short peptides. The pathway for constructing this net involves two cell compartments: cytoplasm and periplasmic space. The pathway starts with a beta-D-fructofuranose going through a mannose PTS permease, phosphorylating the compund and producing a beta-D-fructofuranose 6 phosphate. This compound can be obtained from the glycolysis and pyruvate dehydrogenase or from an isomerization reaction of Beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase.The compound Beta-D-fructofuranose 6 phosphate and L-Glutamine react with a glucosamine fructose-6-phosphate aminotransferase, thus producing a glucosamine 6-phosphate and a l-glutamic acid. The glucosamine 6-phosphate interacts with phosphoglucosamine mutase in a reversible reaction producing glucosamine-1P. Glucosamine-1p and acetyl coa undergo acetylation throuhg a bifunctional protein glmU releasing Coa and a hydrogen ion and producing a N-acetyl-glucosamine 1-phosphate. Glmu, being a bifunctional protein, follows catalyze the interaction of N-acetyl-glucosamine 1-phosphate, hydrogen ion and UTP into UDP-N-acetylglucosamine and pyrophosphate. UDP-N-acetylglucosamine then interacts with phosphoenolpyruvic acid and a UDP-N acetylglucosamine 1- carboxyvinyltransferase realeasing a phosphate and the compound UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate. This compound undergoes a NADPH dependent reduction producing a UDP-N-acetyl-alpha-D-muramate through a UDP-N-acetylenolpyruvoylglucosamine reductase. UDP-N-acetyl-alpha-D-muramate and L-alanine react in an ATP-mediated ligation through a UDP-N-acetylmuramate-alanine ligase releasing an ADP, hydrogen ion, a phosphate and a UDP-N-acetylmuramoyl-L-alanine. This compound interacts with D-glutamic acid and ATP through UDP-N-acetylmuramoylalanine-D-glutamate ligase releasing ADP, A phosphate and UDP-N-acetylmuramoyl-L-alanyl-D-glutamate. The latter compound then interacts with meso-diaminopimelate in an ATP mediated ligation through a UDP-N-acetylmuramoylalanine-D-glutamate-2,6-diaminopimelate ligase resulting in ADP, phosphate, hydrogen ion and UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate. This compound in turn with D-alanyl-D-alanine react in an ATP-mediated ligation through UDP-N-Acetylmuramoyl-tripeptide-D-alanyl-D-alanine ligase to produce UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine and hydrogen ion, ADP, phosphate. UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine interacts with di-trans,octa-cis-undecaprenyl phosphate through a phospho-N-acetylmuramoyl-pentapeptide-transferase, resulting in UMP and N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol which in turn reacts with a UDP-N-acetylglucosamine through a N-acetylglucosaminyl transferase to produce a hydrogen, UDP and Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutaminyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine. This compound ends the cytoplasmic part of the pathway. Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutaminyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine is transported through a lipi II flippase. Once in the periplasmic space, the compound reacts with a penicillin binding protein 1A prodducing a peptidoglycan dimer, a hydrogen ion, and UDP. The peptidoglycan dimer then reacts with a penicillin binding protein 1B producing a peptidoglycan with D,D, cross-links and a D-alanine.PW002062Metabolicalanine biosynthesis IALANINE-VALINESYN-PWYUDP-<i>N</i>-acetylmuramoyl-pentapeptide biosynthesis III (<i>meso</i>-DAP-containing)PWY-6387alanine degradation IALADEG-PWYpeptidoglycan biosynthesis I (<I>meso</I>-diaminopimelate containing)PEPTIDOGLYCANSYN-PWYSpecdb::CMs2623Specdb::CMs38016Specdb::CMs148378Specdb::NmrOneD1679Specdb::NmrOneD5005Specdb::NmrOneD147290Specdb::NmrOneD147291Specdb::NmrOneD147292Specdb::NmrOneD147293Specdb::NmrOneD147294Specdb::NmrOneD147295Specdb::NmrOneD147296Specdb::NmrOneD147297Specdb::NmrOneD147298Specdb::NmrOneD147299Specdb::NmrOneD147300Specdb::NmrOneD147301Specdb::NmrOneD147302Specdb::NmrOneD147303Specdb::NmrOneD147304Specdb::NmrOneD147305Specdb::NmrOneD147306Specdb::NmrOneD147307Specdb::NmrOneD147308Specdb::NmrOneD147309Specdb::MsMs1510Specdb::MsMs1511Specdb::MsMs1512Specdb::MsMs5179Specdb::MsMs5180Specdb::MsMs5181Specdb::MsMs5182Specdb::MsMs5183Specdb::MsMs5184Specdb::MsMs5185Specdb::MsMs178554Specdb::MsMs178555Specdb::MsMs178556Specdb::MsMs180873Specdb::MsMs180874Specdb::MsMs180875Specdb::MsMs437094Specdb::MsMs437095Specdb::MsMs440036Specdb::MsMs440120Specdb::MsMs445521Specdb::MsMs445522Specdb::MsMs445523Specdb::MsMs445524Specdb::MsMs445525Specdb::NmrTwoD1620HMDB013107108064234C0013315570D-ALANINEDALD-AlanineKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Winder, 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 80:2939-2948.18331064Hamase K, Konno R, Morikawa A, Zaitsu K: Sensitive determination of D-amino acids in mammals and the effect of D-amino-acid oxidase activity on their amounts. Biol Pharm Bull. 2005 Sep;28(9):1578-84.16141519D'Aniello A, Vetere A, Fisher GH, Cusano G, Chavez M, Petrucelli L: Presence of D-alanine in proteins of normal and Alzheimer human brain. Brain Res. 1992 Oct 2;592(1-2):44-8.1450921Fukushima T, Santa T, Homma H, Nagatomo R, Imai K: Determination of D-amino acids in serum from patients with renal dysfunction. Biol Pharm Bull. 1995 Aug;18(8):1130-2.8535409Nagata Y, Masui R, Akino T: The presence of free D-serine, D-alanine and D-proline in human plasma. Experientia. 1992 Oct 15;48(10):986-8.1426150Fisher GH, D'Aniello A, Vetere A, Padula L, Cusano GP, Man EH: Free D-aspartate and D-alanine in normal and Alzheimer brain. Brain Res Bull. 1991 Jun;26(6):983-5.1933416http://hmdb.ca/system/metabolites/msds/000/001/172/original/HMDB01310.pdf?1358894033Penicillin-binding protein 1AP02918PBPA_ECOLImrcAhttp://ecmdb.ca/proteins/P02918.xmlPenicillin-binding protein 1BP02919PBPB_ECOLImrcBhttp://ecmdb.ca/proteins/P02919.xmlD-alanine--D-alanine ligase BP07862DDLB_ECOLIddlBhttp://ecmdb.ca/proteins/P07862.xmlAlanine racemase, biosyntheticP0A6B4ALR1_ECOLIalrhttp://ecmdb.ca/proteins/P0A6B4.xmlD-amino acid dehydrogenase small subunitP0A6J5DADA_ECOLIdadAhttp://ecmdb.ca/proteins/P0A6J5.xmlD-alanine--D-alanine ligase AP0A6J8DDLA_ECOLIddlAhttp://ecmdb.ca/proteins/P0A6J8.xmlSerine hydroxymethyltransferaseP0A825GLYA_ECOLIglyAhttp://ecmdb.ca/proteins/P0A825.xmlPeptidoglycan synthase ftsIP0AD68FTSI_ECOLIftsIhttp://ecmdb.ca/proteins/P0AD68.xmlAlanine racemase, catabolicP29012ALR2_ECOLIdadXhttp://ecmdb.ca/proteins/P29012.xmlLow specificity L-threonine aldolaseP75823LTAE_ECOLIltaEhttp://ecmdb.ca/proteins/P75823.xmlMurein tetrapeptide carboxypeptidaseP76008LDCA_ECOLIldcAhttp://ecmdb.ca/proteins/P76008.xmlD-alanyl-D-alanine carboxypeptidase dacCP08506DACC_ECOLIdacChttp://ecmdb.ca/proteins/P08506.xmlD-alanyl-D-alanine carboxypeptidase dacDP33013DACD_ECOLIdacDhttp://ecmdb.ca/proteins/P33013.xmlPenicillin-binding protein 2P0AD65PBP2_ECOLImrdAhttp://ecmdb.ca/proteins/P0AD65.xmlD-alanyl-D-alanine carboxypeptidase dacAP0AEB2DACA_ECOLIdacAhttp://ecmdb.ca/proteins/P0AEB2.xmlD-alanyl-D-alanine dipeptidaseP77790DDPX_ECOLIddpXhttp://ecmdb.ca/proteins/P77790.xmlD-alanyl-D-alanine carboxypeptidase dacBP24228DACB_ECOLIdacBhttp://ecmdb.ca/proteins/P24228.xmlUncharacterized amino-acid ABC transporter ATP-binding protein yecCP37774YECC_ECOLIyecChttp://ecmdb.ca/proteins/P37774.xmlInner membrane amino-acid ABC transporter permease protein yecSP0AFT2YECS_ECOLIyecShttp://ecmdb.ca/proteins/P0AFT2.xmlD-serine/D-alanine/glycine transporterP0AAE0CYCA_ECOLIcycAhttp://ecmdb.ca/proteins/P0AAE0.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmltwo linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) > D-Alanine + two disacharide linked murein units, pentapeptide crosslinked tetrapeptide (A2pm->D-ala) (middle of chain)three linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) >2 D-Alanine + three disacharide linked murein units (pentapeptide crosslinked tetrapeptide (A2pm->D-ala) tetrapeptide corsslinked tetrapeptide (A2pm->D-ala)) (middle of chain)2 D-Alanine + Adenosine triphosphate <> ADP + D-Alanyl-D-alanine + Hydrogen ion + PhosphateR01150DALADALALIG-RXNWater + three disacharide linked murein units (pentapeptide crosslinked tetrapeptide (A2pm->D-ala) tetrapeptide corsslinked tetrapeptide (A2pm->D-ala)) (middle of chain) > D-Alanine + three disacharide linked murein units (tetrapeptide crosslinked tetrapeptide (A2pm->D-ala) & tetrapeptide corsslinked tetrapeptide (A2pm->D-ala)) (middle of chain)Water + two disacharide linked murein units, pentapeptide crosslinked tetrapeptide (A2pm->D-ala) (middle of chain) > D-Alanine + two disacharide linked murein units, tetrapeptide corsslinked tetrapeptide (A2pm->D-ala) (middle of chain)Water + two linked disacharide pentapeptide and tetrapeptide murein units (uncrosslinked, middle of chain) > D-Alanine + two linked disacharide tetrapeptide murein units (uncrosslinked, middle of chain)Water + two linked disacharide pentapeptide and tripeptide murein units (uncrosslinked, middle of chain) > D-Alanine + two linked disacharide tetrapeptide and tripeptide murein units (uncrosslinked, middle of chain)Water + two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) > D-Alanine + two linked disacharide pentapeptide and tetrapeptide murein units (uncrosslinked, middle of chain)L-Alanine <> D-AlanineR00401ALARACECAT-RXND-Alanine + Pyridoxal 5'-phosphate > Pyridoxamine 5'-phosphate + Pyruvic acidRXN0-5240D-Alanine + FAD + Water > FADH2 + Ammonium + Pyruvic acidWater + 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-diaminoheptanedioate1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptideL-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + D-AlanineN-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptideD-Alanyl-D-alanine + Water >2 D-Alanine3.4.13.22-RXNAdenosine triphosphate + 2 D-Alanine <> ADP + Phosphate + D-Alanyl-D-alanineR01150D-Alanine + Pyridoxal 5'-phosphate <> Pyruvic acid + Pyridoxamine 5'-phosphateRXN0-5240peptidoglycan tetrapeptide, glycan chain 2 + peptidoglycan tetrapeptide, glycan chain 1 > peptidoglycan DAP-DAP crosslink + D-AlanineRXN0-5402D-Alanyl-D-alanine + Water > D-Alanine3.4.13.22-RXNa lipid II + Water a <i>N</i>-acetylglucosamine--<i>N</i>-acetylmuramyl-(tetrapeptide) pyrophosphoryl-undecaprenol + D-Alanine3.4.16.4-RXND-Alanine + Adenosine triphosphate > Hydrogen ion + D-Alanyl-D-alanine + Phosphate + ADPDALADALALIG-RXNan electron-transfer-related quinone + Water + D-Alanine > an electron-transfer-related quinol + Ammonium + Pyruvic acidDALADEHYDROG-RXNa peptidoglycan dimer (<I>meso</I>-diaminopimelate containing) + Water > a peptidoglycan with D,D cross-links (<I>meso</I>-diaminopimelate containing) + Undecaprenyl diphosphate + D-AlanineRXN-11302L-Ala-gamma-D-Glu-DAP-D-Ala + Water L-Ala-gamma-D-Glu-Dap + D-AlanineRXN0-5227L-Alanine > D-AlanineAdenosine triphosphate + 2 D-Alanine > ADP + Inorganic phosphate + D-Alanyl-D-alanineGlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine + Water > GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate + D-AlanineD-Alanyl-D-alanine + Water <> D-AlanineR07651 L-Alanine + L-Alanine <> D-AlaninePW_R002512L-Alanine + L-Alanine > D-AlaninePW_R0037322 D-Alanine + Adenosine triphosphate > D-Alanyl-D-alanine + Adenosine diphosphate + Phosphate + ADPPW_R002513D-Alanine + Water + Quinone > Ammonium + Pyruvic acid + HydroquinonePW_R002664D-Alanine + Water + an electron-transfer quinone > Ammonium + Pyruvic acid + electron-transfer quinolPW_R003733 a peptidoglycan dimer (meso-diaminopimelate containing) > D-Alanine + a peptidoglycan with D,D cross-links (meso-diaminopimelate containing)PW_R0034552 D-Alanine + Adenosine triphosphate <> ADP + D-Alanyl-D-alanine + Hydrogen ion + PhosphateAdenosine triphosphate + 2 D-Alanine <> ADP + Phosphate + D-Alanyl-D-alanineL-Alanine <> D-Alanine2 D-Alanine + Adenosine triphosphate <> ADP + D-Alanyl-D-alanine + Hydrogen ion + PhosphateL-Alanine <> D-Alanine