Biosynthesis of β-Lactam Antibiotics

摘要: Penicillins are N-acyl derivatives of 6-aminopenicillanic acid (6-APA) (I), which has a fused β-lactam-thiazolidine ring system (see Fig. 1). Penicillium chrysogenum produces 6-APA, isopenicillin N (Fig. 2) (which δ-linked L-α-aminoadipyl side chain \( [(II),\;{\text{RCO = }}{}^ - {O_2}CCH(\mathop {\text{N}}\limits^ + {H_3}){(C{H_2})_3}CO]\,\,\, \) and number penicillins with non-polar chains [RCO in (II)] derived from mono substituted acetic acids whose nature depends on the precursors present fermentation medium. For example, when phenoxyacetic is added, phenoxymethylpenicillin (penicillin V) produced [(II), RCO C6H5OCH2CO]. At least eight other fungal genera known to produce this manner (Kitano et al., 1975).