| Identification | More | [Name]
D-Alanyl-D-alanine | [CAS]
923-16-0 | [Synonyms]
D-ALA-D-ALA
D-ALANYL-D-ALANINE
H-D-ALA-D-ALA-OH
(2R)-2-[[(2R)-2-aminopropanoyl]amino]propanoic acid
(R)-N-(D-Alanyl)-2-methylglycine
D-Ala-D-Ala-OH
N-(D-Alanyl)-D-alanine | [Molecular Formula]
C6H12N2O3 | [MDL Number]
MFCD00066038 | [Molecular Weight]
160.17 | [MOL File]
923-16-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
120 °C | [Boiling point ]
402.6±30.0 °C(Predicted) | [density ]
1.208±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Acetonitrile: Slightly Soluble
Water: Slightly Soluble | [form ]
Solid | [pka]
3.16±0.10(Predicted) | [color ]
White to off-white | [InChI]
1S/C6H12N2O3/c1-3(7)5(9)8-4(2)6(10)11/h3-4H,7H2,1-2H3,(H,8,9)(H,10,11)/t3-,4-/m1/s1 | [InChIKey]
DEFJQIDDEAULHB-QWWZWVQMSA-N | [SMILES]
C[C@@H](N)C(=O)N[C@H](C)C(O)=O | [CAS DataBase Reference]
923-16-0(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white powder | [Uses]
D-Ala-D-Ala is a bacterial endogenous metabolite. D-Ala-D-Ala constitutes the terminus of the peptide part of the peptidoglycan monomer unit and is involved in the transpeptidation reaction as the substrate. D-Ala-D-Ala is catalyzed by D-Alanine-D-Alanine ligase[1][2][3]. | [Definition]
ChEBI: D-alanyl-D-alanine is a dipeptide comprising D-alanine with a D-alanyl residue attached to the alpha-nitrogen. It is a component of bacterial peptidoglycan and forms an important target for development of antibacterial drugs. It has a role as an Escherichia coli metabolite. It is a tautomer of a D-alanyl-D-alanine zwitterion. | [Biological Activity]
D-Ala-D-Ala is found in the stem termini of peptidoglycan side-chain pentapeptide found in the cell walls of gram positive bacteria. The D-ala-d-ala stem termini is the site of interaction of glycopeptide antibiotics such as vancomycin and teicoplanin. D-ala-D-ala is a substrate used to study kinetics of UDPMurNAc-tripeptide D-alanyl-D-alanine-adding (ligase) enzyme.''D-Ala-D-Alaa terminus moiety of bacterial peptidoglycansis used for affinity chromatography and binding mechanism studies of antibiotics such as teicoplaninristocetinvancomycin. | [IC 50]
Microbial Metabolite | [References]
[1] Kitamura Y, et al. Structure of D-alanine-D-alanine ligase from Thermus thermophilus HB8: cumulative conformational change and enzyme-ligand interactions. Acta Crystallogr D Biol Crystallogr. 2009 Oct;65(Pt 10):1098-106. DOI:10.1107/S0907444909029710
[2] Tytgat I, et al. DD-ligases as a potential target for antibiotics: past, present and future. Curr Med Chem. 2009;16(20):2566-80. DOI:10.2174/092986709788682029
[3] Trivedi RR, et al. Mechanical Genomic Studies Reveal the Role of d-Alanine Metabolism in Pseudomonas aeruginosa Cell Stiffness. mBio. 2018 Sep 11;9(5):e01340-18. DOI:10.1128/mBio.01340-18 |
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