ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Alanine derivatives D-Alanyl-D-alanine

D-Alanyl-D-alanine

Product NameD-Alanyl-D-alanine
CAS923-16-0
MFC6H12N2O3
MW160.17
EINECS
MOL File923-16-0.mol

Chemical Properties

Melting point	120 °C
Boiling point	402.6±30.0 °C(Predicted)
Density	1.208±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,2-8°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)

Safety Information

WGK Germany	3
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

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-Ala, a terminus moiety of bacterial peptidoglycans, is used for affinity chromatography and binding mechanism studies of antibiotics such as teicoplanin, ristocetin, vancomycin.

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
[4] C G MARSHALL. D-Ala-D-Ala ligases from glycopeptide antibiotic-producing organisms are highly homologous to the enterococcal vancomycin-resistance ligases VanA and VanB.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1997, 94 12: 6480-6483. DOI: 10.1073/pnas.94.12.6480

D-Alanyl-D-alanine

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