Penicillins and Cephalosporins

  • E. P. Abraham
  • G. G. F. Newton
Chapter
Part of the Antibiotics book series (ANTIBIOTICS)

Abstract

The penicillins have the general structure (I) and are N-acyl derivatives of 6-aminopenicillanic acid (6-APA, II). During the early chemical work on penicillin it was found that the substance being studied in Oxford differed in its acyl side-chain from that studied in the U.S.A. (Clarke, Johnson and Robinson, 1949; Abraham, 1949). In the former (2-pentenylpenicillin) R was CH3CH2CH =CH · CH2 and in the latter (benzylpenicillin) R was C6H5CH2. Subsequent work showed that many different penicillins could be produced byPenicillium chrysogenum by the addition of appropriate side-chain precursors to fermentation media (Behrens et al., 1948; Thorn and Johnson, 1950). Most of the precursors which were effective in this way were monosubstituted acetic acids or their derivatives (R · CH2CO2H) in which R was a relatively non-polar aliphatic or aromatic grouping. Later, certain species of Cephalosporium and members of the genus Emericellopsis were shown to produce a penicillin with a zwitterionic side-chain derived from D-α-aminoadipic acid (Abraham, 1962). This substance, which was first named cephalosporin N or synnematin B and later penicillin N, has also been reported to be produced by a Streptomyces sp. (Miller, Stapley and Charet, 1962) and by Paecilomyces persicinus (Pisano et al., 1960). Following the discovery of penicillin N, it was found that 6-aminopenicillanic acid (II) (Batchelor et al., 1959) and isopenicillin N, whose side-chain (RCO in I) is derived from L-α-aminoadipic acid (Flynn et al., 1962; Cole and Batchelor, 1963), can be produced in significant amounts byP. chrysogenum in fermentations to which no side-chain precursor is added.

Keywords

Adipic Acid Penicillium Chrysogenum Benzylpenicillin Acylase Penicillin Production Penicillanic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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  • E. P. Abraham
  • G. G. F. Newton

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