A dipeptide moiety of bacterial peptidoglycan
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D-Ala-D-Ala

Item No. 39648

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
D-alanyl-D-alanine
CAS Number
923-16-0
Synonyms
  • DADA
Molecular Formula
C6H12N2O3
Formula Weight
160.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly SolubleWater: Slightly Soluble
SMILES
C[C@@H](NC([C@H](N)C)=O)C(O)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $142

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    500 mg

    $270

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    1 g

    $511

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    Cayman Chemical
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    Product Description

    D-Ala-D-Ala is the terminal dipeptide moiety of peptidoglycan in bacterial cell walls and a target of certain antibacterial agents.1 Replacement of D-Ala-D-Ala with D-Ala-D-lactate by the combined activity of the enterococcal gene products VanA, VanH, and VanX reduces the affinity of the antibiotic vancomycin (Item No. 15327) for the peptidoglycan and is responsible for vancomycin resistance.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Marshall, C.G., Broadhead, G.K., Leskiw, B.K., et al. D-Ala-D-Ala ligases from glycopeptide antibiotic-producing organisms are highly homologous to the enterococcal vancomycin-resistance ligases VanA and VanB. Proc. Natl. Acad. Sci. USA. 94(12), 6480-6483 (1997).