• 6-Aminopenicillanic acid

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SKU: A089

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Description

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 by Scientists at The 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 of Ampicillin and Amoxicillin. 

    CAS Number

    551-16-6

    Molecular Formula

    C8H12N2O3S

    Molecular Weight

    216.26

    Mechanism of Action

    6-Aminopenicillanic acid interferes with the synthesis of bacterial cell walls of Gram-positive bacteria.

    Spectrum

    6-Aminopenicillanic acid is effective against Gram-positive bacteria.

Applications

    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

Specifications

    Appearance

    White or almost white crystalline powder

    Source

    Penicillium

    Impurity Profile

    Penicillin G K: Not more than 0.1%
    Phenylacetic Acid: Not more than 0.1%

    Absorbance

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

    pH

    3.5 – 4.5

    Optical Rotation

    +265.0°-+285.0°

    Assay

    Not less than 96.0%

    Loss on Drying

    Not more than 0.20%

References

    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

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