6-Aminopenicillanic Acid (syn: (+)-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-Aminopenicillanic Acid, 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.|
|Impurity Profile||Penicillin G K: ≤ 0.1%
Phenylacetic Acid: ≤ 0.1%
|Absorbance||425nm - <0.025; 500nm - ≥ 90.0%|
Batchelor FR, Doyle FP, Nayler JH and Rolinson GN (1959) Synthesis of penicillin: 6-Amnopenicillanic Acid in penicillin fermentations. Nature 183(4656):257-258