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A0912

Sigma-Aldrich

D-Ala-D-Ala

≥99%

Synonyme(s) :

D-alanyl-D-Alanine

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About This Item

Formule empirique (notation de Hill):
C6H12N2O3
Numéro CAS:
923-16-0
Poids moléculaire :
160.17
Numéro MDL:
MFCD00066038
Code UNSPSC :
12352202
ID de substance PubChem :
24890468
Nomenclature NACRES :
NA.26

product name

D-Ala-D-Ala,

Pureté

≥99%

Niveau de qualité

200

Forme

powder

Couleur

white to off-white

Température de stockage

−20°C

Chaîne SMILES 

C[C@@H](N)C(=O)N[C@H](C)C(O)=O

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

Clé InChI

DEFJQIDDEAULHB-QWWZWVQMSA-N

Application


  • Binding Mode-Based Physicochemical Screening Method Using d-Ala-d-Ala Silica Gel and Chemical Modification Approach to Facilitate Discovery of New Macrolactams, Banglactams A and B, from Nonomuraea bangladeshensis K18-0086.: Describes a novel screening method employing D-Ala-D-Ala silica gel to discover new macrolactams with potential antibacterial properties. This technique aids in identifying compounds that inhibit bacterial cell wall synthesis (Kimishima et al., 2024).

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

I Tytgat et al.
Current medicinal chemistry, 16(20), 2566-2580 (2009-07-16)
DD-ligases catalyze the synthesis of the D-Ala-D-Ala and D-Ala-D-Ser dipeptides or the D Ala-D-Lac depsipeptide in an early step of peptidoglycan synthesis. Their function is essential for bacterial growth and specific to bacteria, making them attractive targets for the development
Gareth A Prosser et al.
Antimicrobial agents and chemotherapy, 60(10), 6091-6099 (2016-08-03)
The increasing global prevalence of drug resistance among many leading human pathogens necessitates both the development of antibiotics with novel mechanisms of action and a better understanding of the physiological activities of preexisting clinically effective drugs. Inhibition of peptidoglycan (PG)
Yoshiaki Kitamura et al.
Acta crystallographica. Section D, Biological crystallography, 65(Pt 10), 1098-1106 (2009-09-23)
D-Alanine-D-alanine ligase (Ddl) is one of the key enzymes in peptidoglycan biosynthesis and is an important target for drug discovery. The enzyme catalyzes the condensation of two D-Ala molecules using ATP to produce D-Ala-D-Ala, which is the terminal peptide of
Ivona Pavkova et al.
Frontiers in cellular and infection microbiology, 7, 503-503 (2018-01-13)
The DsbA homolog of
Vivek K Mutalik et al.
PLoS biology, 18(10), e3000877-e3000877 (2020-10-14)
Bacteriophages (phages) are critical players in the dynamics and function of microbial communities and drive processes as diverse as global biogeochemical cycles and human health. Phages tend to be predators finely tuned to attack specific hosts, even down to the
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