SKU: A089  / 
    CAS Number: 551-16-6

    6-Aminopenicillanic acid

    $44.56 - $72.41

    6-Aminopenicillanic Acid or (+)-6-Aminopenicillanic Acid (6-APA) is an organic dipeptide and the  chemical core or "nucleus" of penicillin antibiotics.  It was discovered in 1958  (Beecham Group, UK).  It is produced from Penicillin by penicillin amidase.  6-APA, a β-lactam, is used as a starting compound for synthesis of semisynthetic Penicillins and may be substituted at the 6-amino position, resulting in a variety of antibacterial properties.  It is a precursor to Ampicillin and Amoxicillin. 

    Application 6-aminopenicillanic acid can be used as a a starting material to synthesize penicillin antibiotics. The compound reacts with higher amino acid Schiff bases to form the corresponding β-lactam derivatives.
    Mechanism of Action 6-Aminopenicillanic Acid interferes with the synthesis of bacterial cell walls of Gram-positive bacteria.
    Eukaryotic Cell Culture Applications

    The coating of (+)-6-Aminopenicillanic Acid on silver nanoparticles (6APA-AgNPs), can impart an ability to detect chromium (IV) in human erythrocytes.

    Spectrum Gram-positive bacteria.
    Impurity Profile Penicillin G K: Not more than 0.1%
    Phenylacetic Acid: Not more than 0.1%
    Molecular Formula

    C8H12N2O3S

    Absorbance 425nm - Less than 0.025; Transmittance: 500nm - Not less than 90.0%
    References

    Batchelor FR, Doyle FP, Nayler JH and Rolinson GN (1959)  Synthesisi of penicillin: 6-Amnopenicillanic acid in penicillin fermentations. Nature 183(4656):257-258

    Parmar A, Kumar H, Marwaha SS and Kennedy JF (2000)  Advances in enzymatic transformation of penicillins to 6-Aminopenicillanic acid (6-APA).  Biotechnol Advances 18(4):289-301

    Rolinson GN and Geddes AM (2007) Erratum to “The 50th anniversary of the discovery of 6-aminopenicillanic acid (6-APA)’” Int. J. Antimicrob. Agents 29 (5):613