2.0 2012-05-31 13:49:38 -0600 2015-09-13 12:56:10 -0600 ECMDB01310 M2MDB000333 D-Alanine D-Alanine is an amino acid and one of the most important molecules in living organisms. It has a chiral carbon at a -position. (R)-Alanine D(-)-a -Alanine D(-)-a-Alanine D(-)-alpha-Alanine D(-)-α-Alanine D-(-)-Alanine D-2-Aminopropionate D-2-Aminopropionic acid D-a-Alanine D-Ala D-Alanine D-alpha-Alanine D-α-Alanine Delta-(-)-Alanine Delta-2-Aminopropionate Delta-2-Aminopropionic acid delta-a-Alanine Delta-Alanine Delta-alpha-Alanine Dl-Alanine δ-(-)-Alanine δ-2-Aminopropionate δ-2-Aminopropionic acid δ-a-Alanine δ-Alanine δ-α-Alanine C3H7NO2 89.0932 89.047678473 (2R)-2-aminopropanoic acid D-alanine 338-69-2 C[C@@H](N)C(O)=O InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1 QNAYBMKLOCPYGJ-UWTATZPHSA-N Solid Cytosol Extra-organism Periplasm logp -3.05 ALOGPS logs 0.70 ALOGPS solubility 4.47e+02 g/l ALOGPS melting_point 292 oC logp -2.8 ChemAxon pka_strongest_acidic 2.47 ChemAxon pka_strongest_basic 9.48 ChemAxon iupac (2R)-2-aminopropanoic acid ChemAxon average_mass 89.0932 ChemAxon mono_mass 89.047678473 ChemAxon smiles C[C@@H](N)C(O)=O ChemAxon formula C3H7NO2 ChemAxon inchi InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1 ChemAxon inchikey QNAYBMKLOCPYGJ-UWTATZPHSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 20.5 ChemAxon polarizability 8.54 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Vitamin B6 metabolism ec00750 Peptidoglycan biosynthesis ec00550 D-Alanine metabolism L-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. PW000768 ec00473 Metabolic Metabolic pathways eco01100 Vancomycin resistance eco01502 L-alanine metabolism L-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. PW000788 Metabolic inner membrane transport list 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 added PW000786 Metabolic peptidoglycan biosynthesis I Peptidoglycan 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. PW000906 Metabolic peptidoglycan biosynthesis I 2 Peptidoglycan 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. PW002062 Metabolic alanine biosynthesis I ALANINE-VALINESYN-PWY UDP-<i>N</i>-acetylmuramoyl-pentapeptide biosynthesis III (<i>meso</i>-DAP-containing) PWY-6387 alanine degradation I ALADEG-PWY peptidoglycan biosynthesis I (<I>meso</I>-diaminopimelate containing) PEPTIDOGLYCANSYN-PWY Specdb::CMs 2623 Specdb::CMs 38016 Specdb::CMs 148378 Specdb::NmrOneD 1679 Specdb::NmrOneD 5005 Specdb::NmrOneD 147290 Specdb::NmrOneD 147291 Specdb::NmrOneD 147292 Specdb::NmrOneD 147293 Specdb::NmrOneD 147294 Specdb::NmrOneD 147295 Specdb::NmrOneD 147296 Specdb::NmrOneD 147297 Specdb::NmrOneD 147298 Specdb::NmrOneD 147299 Specdb::NmrOneD 147300 Specdb::NmrOneD 147301 Specdb::NmrOneD 147302 Specdb::NmrOneD 147303 Specdb::NmrOneD 147304 Specdb::NmrOneD 147305 Specdb::NmrOneD 147306 Specdb::NmrOneD 147307 Specdb::NmrOneD 147308 Specdb::NmrOneD 147309 Specdb::MsMs 1510 Specdb::MsMs 1511 Specdb::MsMs 1512 Specdb::MsMs 5179 Specdb::MsMs 5180 Specdb::MsMs 5181 Specdb::MsMs 5182 Specdb::MsMs 5183 Specdb::MsMs 5184 Specdb::MsMs 5185 Specdb::MsMs 178554 Specdb::MsMs 178555 Specdb::MsMs 178556 Specdb::MsMs 180873 Specdb::MsMs 180874 Specdb::MsMs 180875 Specdb::MsMs 437094 Specdb::MsMs 437095 Specdb::MsMs 440036 Specdb::MsMs 440120 Specdb::MsMs 445521 Specdb::MsMs 445522 Specdb::MsMs 445523 Specdb::MsMs 445524 Specdb::MsMs 445525 Specdb::NmrTwoD 1620 HMDB01310 71080 64234 C00133 15570 D-ALANINE DAL D-Alanine 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 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 Hamase 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. 16141519 D'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. 1450921 Fukushima 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. 8535409 Nagata 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. 1426150 Fisher 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. 1933416 http://hmdb.ca/system/metabolites/msds/000/001/172/original/HMDB01310.pdf?1358894033 Penicillin-binding protein 1A P02918 PBPA_ECOLI mrcA http://ecmdb.ca/proteins/P02918.xml Penicillin-binding protein 1B P02919 PBPB_ECOLI mrcB http://ecmdb.ca/proteins/P02919.xml D-alanine--D-alanine ligase B P07862 DDLB_ECOLI ddlB http://ecmdb.ca/proteins/P07862.xml Alanine racemase, biosynthetic P0A6B4 ALR1_ECOLI alr http://ecmdb.ca/proteins/P0A6B4.xml D-amino acid dehydrogenase small subunit P0A6J5 DADA_ECOLI dadA http://ecmdb.ca/proteins/P0A6J5.xml D-alanine--D-alanine ligase A P0A6J8 DDLA_ECOLI ddlA http://ecmdb.ca/proteins/P0A6J8.xml Serine hydroxymethyltransferase P0A825 GLYA_ECOLI glyA http://ecmdb.ca/proteins/P0A825.xml Peptidoglycan synthase ftsI P0AD68 FTSI_ECOLI ftsI http://ecmdb.ca/proteins/P0AD68.xml Alanine racemase, catabolic P29012 ALR2_ECOLI dadX http://ecmdb.ca/proteins/P29012.xml Low specificity L-threonine aldolase P75823 LTAE_ECOLI ltaE http://ecmdb.ca/proteins/P75823.xml Murein tetrapeptide carboxypeptidase P76008 LDCA_ECOLI ldcA http://ecmdb.ca/proteins/P76008.xml D-alanyl-D-alanine carboxypeptidase dacC P08506 DACC_ECOLI dacC http://ecmdb.ca/proteins/P08506.xml D-alanyl-D-alanine carboxypeptidase dacD P33013 DACD_ECOLI dacD http://ecmdb.ca/proteins/P33013.xml Penicillin-binding protein 2 P0AD65 PBP2_ECOLI mrdA http://ecmdb.ca/proteins/P0AD65.xml D-alanyl-D-alanine carboxypeptidase dacA P0AEB2 DACA_ECOLI dacA http://ecmdb.ca/proteins/P0AEB2.xml D-alanyl-D-alanine dipeptidase P77790 DDPX_ECOLI ddpX http://ecmdb.ca/proteins/P77790.xml D-alanyl-D-alanine carboxypeptidase dacB P24228 DACB_ECOLI dacB http://ecmdb.ca/proteins/P24228.xml Uncharacterized amino-acid ABC transporter ATP-binding protein yecC P37774 YECC_ECOLI yecC http://ecmdb.ca/proteins/P37774.xml Inner membrane amino-acid ABC transporter permease protein yecS P0AFT2 YECS_ECOLI yecS http://ecmdb.ca/proteins/P0AFT2.xml D-serine/D-alanine/glycine transporter P0AAE0 CYCA_ECOLI cycA http://ecmdb.ca/proteins/P0AAE0.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml two 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 + Phosphate R01150 DALADALALIG-RXN Water + 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-Alanine R00401 ALARACECAT-RXN D-Alanine + Pyridoxal 5'-phosphate > Pyridoxamine 5'-phosphate + Pyruvic acid RXN0-5240 D-Alanine + FAD + Water > FADH2 + Ammonium + Pyruvic acid 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 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptide L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + D-Alanine N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide D-Alanyl-D-alanine + Water >2 D-Alanine 3.4.13.22-RXN Adenosine triphosphate + 2 D-Alanine <> ADP + Phosphate + D-Alanyl-D-alanine R01150 D-Alanine + Pyridoxal 5'-phosphate <> Pyruvic acid + Pyridoxamine 5'-phosphate RXN0-5240 peptidoglycan tetrapeptide, glycan chain 2 + peptidoglycan tetrapeptide, glycan chain 1 > peptidoglycan DAP-DAP crosslink + D-Alanine RXN0-5402 D-Alanyl-D-alanine + Water > D-Alanine 3.4.13.22-RXN a lipid II + Water a <i>N</i>-acetylglucosamine--<i>N</i>-acetylmuramyl-(tetrapeptide) pyrophosphoryl-undecaprenol + D-Alanine 3.4.16.4-RXN D-Alanine + Adenosine triphosphate > Hydrogen ion + D-Alanyl-D-alanine + Phosphate + ADP DALADALALIG-RXN an electron-transfer-related quinone + Water + D-Alanine > an electron-transfer-related quinol + Ammonium + Pyruvic acid DALADEHYDROG-RXN a peptidoglycan dimer (<I>meso</I>-diaminopimelate containing) + Water > a peptidoglycan with D,D cross-links (<I>meso</I>-diaminopimelate containing) + Undecaprenyl diphosphate + D-Alanine RXN-11302 L-Ala-gamma-D-Glu-DAP-D-Ala + Water L-Ala-gamma-D-Glu-Dap + D-Alanine RXN0-5227 L-Alanine > D-Alanine Adenosine triphosphate + 2 D-Alanine > ADP + Inorganic phosphate + D-Alanyl-D-alanine GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine + Water > GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate + D-Alanine D-Alanyl-D-alanine + Water <> D-Alanine R07651 L-Alanine + L-Alanine <> D-Alanine PW_R002512 L-Alanine + L-Alanine > D-Alanine PW_R003732 2 D-Alanine + Adenosine triphosphate > D-Alanyl-D-alanine + Adenosine diphosphate + Phosphate + ADP PW_R002513 D-Alanine + Water + Quinone > Ammonium + Pyruvic acid + Hydroquinone PW_R002664 D-Alanine + Water + an electron-transfer quinone > Ammonium + Pyruvic acid + electron-transfer quinol PW_R003733 a peptidoglycan dimer (meso-diaminopimelate containing) > D-Alanine + a peptidoglycan with D,D cross-links (meso-diaminopimelate containing) PW_R003455 2 D-Alanine + Adenosine triphosphate <> ADP + D-Alanyl-D-alanine + Hydrogen ion + Phosphate Adenosine triphosphate + 2 D-Alanine <> ADP + Phosphate + D-Alanyl-D-alanine L-Alanine <> D-Alanine 2 D-Alanine + Adenosine triphosphate <> ADP + D-Alanyl-D-alanine + Hydrogen ion + Phosphate L-Alanine <> D-Alanine