Abstract
Extracts containing penicillin acylase were obtained by shaking the mycelium of Fusarium avenaceum and of Penicillium chrysogenum in 0.2 M sodium acetate or sodium chloride solution. The optimum pH for conversion of penicillin V into 6-aminopenicillanic acid (6-APA) by the enzyme of Fusarium was about 7.5, and the reaction velocity was increased by a rise in temperature from 27 to 37 C. Penicillin G and penicillins with an aliphatic side chain were cleaved much less readily than was penicillin V. With the enzyme preparation obtained from a nonpenicillin-producing strain of P. chrysogenum, the reaction rate was higher at pH 8.5 than at pH 7.5 and pH 6.5. The acylase of P. chrysogenum hydrolyzes penicillin V more readily than penicillin G. In a series of aliphatic penicillins, the amount of 6-APA formed through the action of this enzyme increased with the number of carbon atoms of the side chain. Penicillins with a glutaryl or an adipyl group as side chain were unaffected by the enzyme of Fusarium and of Penicillium. No reaction was observed upon incubation of penicillin N (with a D-aminoadipyl side chain) or isopenicillin N (with an L-aminoadipyl side chain) with Fusarium and Penicillium extract. When the carboxy group of the side chain of these penicillins was esterified, formation of 6-APA was observed upon incubation with Penicillium extract, whereas no 6-APA or only very small amounts were obtained by acylase of Fusarium.
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- ARNSTEIN H. R., MORRIS D. The structure of a peptide, containing alpha-aminoadipic acid, cystine and valine, present in the mycelium of Penicillium chrysogenum. Biochem J. 1960 Aug;76:357–361. doi: 10.1042/bj0760357. [DOI] [PMC free article] [PubMed] [Google Scholar]
- BATCHELOR F. R., DOYLE F. P., NAYLER J. H., ROLINSON G. N. Synthesis of penicillin: 6-aminopenicillanic acid in penicillin fermentations. Nature. 1959 Jan 24;183(4656):257–258. doi: 10.1038/183257b0. [DOI] [PubMed] [Google Scholar]
- Brandl E. Zur Kenntnis der Penicillinamidase. Hoppe Seylers Z Physiol Chem. 1965;342(1):86–92. [PubMed] [Google Scholar]
- Brunner R., Röhr M., Zinner M. Zur Biosynthese des Penicillins. Untersuchungen zur enzymatischen Aktivierung von Phenylessigsäure und Phenoxyessigsäure sowie zur Bildung von Penicillin aus 6-Amino-penicillansäure und aktivierter Seitenkettensäure durch Mycelhomogenate und zellfreie Extrakte von Penicillium chrysogenum. Hoppe Seylers Z Physiol Chem. 1968 Jan;349(1):95–103. doi: 10.1515/bchm2.1968.349.1.95. [DOI] [PubMed] [Google Scholar]
- CLARIDGE C. A., LUTTINGER J. R., LEIN J. SPECIFICITY OF PENICILLIN AMIDASES. Proc Soc Exp Biol Med. 1963 Aug-Sep;113:1008–1012. doi: 10.3181/00379727-113-28559. [DOI] [PubMed] [Google Scholar]
- COLE M., BATCHELOR F. R. Aminoadipylpenicillin in penicillin fermentations. Nature. 1963;198:383–384. doi: 10.1038/198383a0. [DOI] [PubMed] [Google Scholar]
- COLE M., ROLINSON G. N. 6-Aminopenicillanic acid. II. Formation of 6-aminopenicillanic acid by Emericellopsis minima (Stolk) and related fungi. Proc R Soc Lond B Biol Sci. 1961 Aug 15;154:490–497. doi: 10.1098/rspb.1961.0046. [DOI] [PubMed] [Google Scholar]
- Cole M. Formation of 6-aminopenicillanic acid, penicillins, and penicillin acylase by various fungi. Appl Microbiol. 1966 Jan;14(1):98–104. doi: 10.1128/am.14.1.98-104.1966. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Erickson R. C., Bennett R. E. Penicillin acylase activity of Penicillium chrysogenum. Appl Microbiol. 1965 Sep;13(5):738–742. doi: 10.1128/am.13.5.738-742.1965. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Erickson R. C., Dean L. D. Acylation of 6-Aminopenicillanic Acid by Penicillium chrysogenum. Appl Microbiol. 1966 Nov;14(6):1047–1048. doi: 10.1128/am.14.6.1047-1048.1966. [DOI] [PMC free article] [PubMed] [Google Scholar]
- HUANG H. T., SETO T. A., SHULL G. M. Distribution and substrate specificity of benzylpenicillin acylase. Appl Microbiol. 1963 Jan;11:1–6. doi: 10.1128/am.11.1.1-6.1963. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Hamilton-Miller J. M. Penicillinacylase. Bacteriol Rev. 1966 Dec;30(4):761–771. doi: 10.1128/br.30.4.761-771.1966. [DOI] [PMC free article] [PubMed] [Google Scholar]
- JARVIS F. G., JOHNSON M. J. The mineral nutrition of Penicillium chrysogenum Q176. J Bacteriol. 1950 Jan;59(1):51–60. doi: 10.1128/jb.59.1.51-60.1950. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Pruess D. L., Johnson M. J. Penicillin acyltransferase in Penicillium chrysogenum. J Bacteriol. 1967 Nov;94(5):1502–1508. doi: 10.1128/jb.94.5.1502-1508.1967. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Sjöberg B., Nathorst-Westfelt L., Ortengren B. Enzymatic hydrolysis of some penicillins and cephalosporins by Escherichia coli acylase. Acta Chem Scand. 1967;21(2):547–551. doi: 10.3891/acta.chem.scand.21-0547. [DOI] [PubMed] [Google Scholar]
- Spencer B. The biosynthesis of penicillins: Acylation of 6-aminopenicillanic acid. Biochem Biophys Res Commun. 1968 Apr 19;31(2):170–175. doi: 10.1016/0006-291x(68)90725-0. [DOI] [PubMed] [Google Scholar]
- WALDSCHMIDT-LEITZ E., BRETZEL G. UBER PENICILLINAMIDASE: REINIGUNG UND EIGENSCHAFTEN. Hoppe Seylers Z Physiol Chem. 1964;337:222–228. doi: 10.1515/bchm2.1964.337.1.222. [DOI] [PubMed] [Google Scholar]