D-Ala-D-Ala A biologically active peptide used for affinity chromatography and binding mechanism studies

D-Ala-D-Ala (CAS 923-16-0)

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Synonym: 2-[(2-ammoniopropanoyl)amino]propanoate; D-alanyl-D-alanine
Application: A biologically active peptide used for affinity chromatography and binding mechanism studies
CAS Number: 923-16-0
Molecular Weight: 160.17
Molecular Formula: C6H12N2O3
* Refer to Certificate of Analysis for lot specific data (including water content).
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D-Ala-D-Ala is a biologically active peptide used for affinity chromatography and binding mechanism studies of antibiotics such as teicoplanin, ristocetin, and vancomycin.


References

1. Quinn, Ryan K., Cianci, Amelia L., Beaudoin, Jennifer A., Sculimbrene, Bianca R., 2010. Synthesis of a D-Ala-D-Ala peptide isostere via olefin cross-metathesis and evaluation of vancomycin binding. Bioorganic & medicinal chemistry letters. 20(15): 4382-5. PMID: 20594838 2. Xie, Jian., Pierce, Joshua G., James, Robert C., Okano, Akinori., Boger, Dale L., 2011. A redesigned vancomycin engineered for dual D-Ala-D-ala And D-Ala-D-Lac binding exhibits potent antimicrobial activity against vancomycin-resistant bacteria. Journal of the American Chemical Society. 133(35): 13946-9. PMID: 21823662 3. Putty, Sandeep., Rai, Aman., Jamindar, Darshan., Pagano, Paul., Quinn, Cheryl L., Mima, Takehiko., Schweizer, Herbert P., Gutheil, William G., 2011. Characterization of d-boroAla as a novel broad-spectrum antibacterial agent targeting d-Ala-d-Ala ligase. Chemical biology & drug design. 78(5): 757-63. PMID: 21827632 4. Xie, Jian., Okano, Akinori., Pierce, Joshua G., James, Robert C., Stamm, Simon., Crane, Christine M., Boger, Dale L., 2012. Total synthesis of [Ψ[C(=S)NH]Tpg4]vancomycin aglycon, [Ψ[C(=NH)NH]Tpg4]vancomycin aglycon, and related key compounds: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding. Journal of the American Chemical Society. 134(2): 1284-97. PMID: 22188323 5. Kwun, Min Jung., Novotna, Gabriela., Hesketh, Andrew R., Hill, Lionel., Hong, Hee-Jeon., 2013. In vivo studies suggest that induction of VanS-dependent vancomycin resistance requires binding of the drug to D-Ala-D-Ala termini in the peptidoglycan cell wall. Antimicrobial agents and chemotherapy. 57(9): 4470-80. PMID: 23836175

Physical State :
Solid
Storage :
Store at -20° C
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
5460362
SMILES :
C[C@H](C(=O)N[C@H](C)C(=O)O)N

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Certificate of Analysis

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