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A0912

Sigma-Aldrich

D-Ala-D-Ala

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Synonym(s):
D-alanyl-D-Alanine
Empirical Formula (Hill Notation):
C6H12N2O3
CAS Number:
Molecular Weight:
160.17
MDL number:
PubChem Substance ID:
NACRES:
NA.26

Assay

≥99%

Quality Level

form

powder

color

white to off-white

storage temp.

−20°C

SMILES string

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

InChI key

DEFJQIDDEAULHB-QWWZWVQMSA-N

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This Item
A950247435D9378
D-Ala-D-Ala

Sigma-Aldrich

A0912

D-Ala-D-Ala

Ala-Ala

Sigma-Aldrich

A9502

Ala-Ala

form

powder

form

powder

form

-

form

powder

color

white to off-white

color

white

color

-

color

-

storage temp.

−20°C

storage temp.

-

storage temp.

2-8°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

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Olatunde P Olademehin et al.
ACS omega, 6(1), 775-785 (2021-01-19)
Vancomycin is a glycopeptide antibiotic produced by Amycolaptopsis orientalis used to treat serious infections by Gram-positive pathogens including methicillin-resistant Staphylococcus aureus. Vancomycin inhibits cell wall biosynthesis by targeting lipid II, which is the membrane-bound peptidoglycan precursor. The heptapeptide aglycon structure
Ivona Pavkova et al.
Frontiers in cellular and infection microbiology, 7, 503-503 (2018-01-13)
The DsbA homolog of
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
Nayeong Kim et al.
BMC microbiology, 21(1), 27-27 (2021-01-20)
Zinc uptake-regulator (Zur)-regulated lipoprotein A (ZrlA) plays a role in bacterial fitness and overcoming antimicrobial exposure in Acinetobacter baumannii. This study further characterized the zrlA gene and its encoded protein and investigated the roles of the zrlA gene in bacterial
Maulik N Thaker et al.
Antimicrobial agents and chemotherapy, 59(3), 1405-1410 (2014-12-17)
Vancomycin-resistant enterococci (VRE) are notorious clinical pathogens restricting the use of glycopeptide antibiotics in the clinic setting. Routine surveillance to detect VRE isolated from patients relies on PCR bioassays and chromogenic agar-based test methods. In recent years, we and others

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