Skip to main content
Biochemical Journal logoLink to Biochemical Journal
. 1975 Dec;151(3):741–746. doi: 10.1042/bj1510741

Behaviour of tritium-labelled isopenicillin N and 6-aminopenicillanic acid as potential penicillin precursors in an extract of Penicillum chrysogenum.

P A Fawcett, J J Usher, E P Abraham
PMCID: PMC1172423  PMID: 175788

Abstract

1. 3H was incorporated into solvent-soluble penicillin from isopenicillin N and 6-aminopenicillanic acid 3H-labelled in the 2beta-methyl group when the labelled compounds were incubated with a crude extract of Penicillum chrysogenum. 2. With a soluble protein fraction of the extract incorporation from isopenicillin N occurred on addition of phenyl-acetyl-CoA. 3. Labelled benzylpenicillin was isolated after incubation of the crude extract with phenylacetyl-CoA and isopenicillin and the addition of unlabelled benzylpenicillin as a carrier. 4. No incorporation of 3H into solvent-soluble penicillin was detected on incubation of these extracts with penicillin N.

Full text

PDF
745

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. 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]
  2. 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]
  3. BRUNO G. A., CHRISTIAN J. E. Note on suitable solvent systems usable in the liquid scintillation counting of animal tissue. J Am Pharm Assoc Am Pharm Assoc. 1960 Aug;49:560–561. doi: 10.1002/jps.3030490820. [DOI] [PubMed] [Google Scholar]
  4. 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]
  5. COLE M., BATCHELOR F. R. Aminoadipylpenicillin in penicillin fermentations. Nature. 1963;198:383–384. doi: 10.1038/198383a0. [DOI] [PubMed] [Google Scholar]
  6. Cole M. Hydrolysis of penicillins and related compounds by the cell-bound penicillin acylase of Escherichia coli. Biochem J. 1969 Dec;115(4):733–739. doi: 10.1042/bj1150733. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Davies R. B., Abraham E. P. Separation, purification and properties of beta-lactamase I and beta-lactamase II from Bacillus cereus 569/H/9. Biochem J. 1974 Oct;143(1):115–127. doi: 10.1042/bj1430115. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. GOA J. A micro biuret method for protein determination; determination of total protein in cerebrospinal fluid. Scand J Clin Lab Invest. 1953;5(3):218–222. doi: 10.3109/00365515309094189. [DOI] [PubMed] [Google Scholar]
  9. Gailey F. B., Stefaniak J. J., Olson B. H., Johnson M. J. A Comparison of Penicillin-producing Strains of Penicillium notatum-chrysogenum. J Bacteriol. 1946 Jul;52(1):129–140. [PMC free article] [PubMed] [Google Scholar]
  10. Gatenbeck S., Brunsberg U. Biosynthesis of penicillins. I. Isolation of a 6-aminopenicillanic acid acyltransferase from Penicillium chrysogenum. Acta Chem Scand. 1968;22(3):1059–1061. doi: 10.3891/acta.chem.scand.22-1059. [DOI] [PubMed] [Google Scholar]
  11. KAUFMANN W., BAUER K. VARIETY OF SUBSTRATES FOR A BACTERIAL BENZYL PENICILLIN-SPLITTING ENZYME. Nature. 1964 Aug 1;203:520–520. doi: 10.1038/203520a0. [DOI] [PubMed] [Google Scholar]
  12. Loder P. B., Abraham E. P. Biosynthesis of peptides containing -aminoadipic acid and cysteine in extracts of a Cephalosporium sp. Biochem J. 1971 Jul;123(3):477–482. doi: 10.1042/bj1230477. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Loder P. B. Selected aspects of the biosynthesis of penicillins and cephalosporins. Postepy Hig Med Dosw. 1972 Jul-Aug;26(4):493–500. [PubMed] [Google Scholar]
  14. NEWTON G. G., ABRAHAM E. P. Degradation, structure and some derivatives of cephalosporin N. Biochem J. 1954 Sep;58(1):103–111. doi: 10.1042/bj0580103. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. 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]
  16. Smith B., Warren S. C., Newton G. G., Abraham E. P. Biosynthesis of penicillin N and cephalosporin C. Antibiotic production and other features of the metabolism of Cephalosporium sp. Biochem J. 1967 Jun;103(3):877–890. doi: 10.1042/bj1030877. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. 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]
  18. THOMAS R. Colorimetric detection of penicillins and cephalosporins on paper. Nature. 1961 Sep 16;191:1161–1163. doi: 10.1038/1911161a0. [DOI] [PubMed] [Google Scholar]
  19. Usher J. J., Loder B., Abraham E. P. Synthesis of tritium-labelled isopenicillin N, penicillin N and 6-aminopenicillanic acid. Biochem J. 1975 Dec;151(3):729–739. doi: 10.1042/bj1510729. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Vanderhaeghe H., Claesen M., Vlietinck A., Parmentier G. Specificity of penicillin acylase of Fusarium and of Penicillium chrysogenum. Appl Microbiol. 1968 Oct;16(10):1557–1563. doi: 10.1128/am.16.10.1557-1563.1968. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES