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. 1975 Dec;8(6):638–642. doi: 10.1128/aac.8.6.638

Presence of δ-(l-α-Aminoadipyl)-l-Cysteinyl-d-Valine in Fermentations of Penicillium chrysogenum

P Adriaens 1, B Meesschaert 1, W Wuyts 1, H Vanderhaeghe 1, H Eyssen 1
PMCID: PMC429440  PMID: 813571

Abstract

Cultures of Penicillium chrysogenum, growth with [35S]sulfate or labeled amino acids, were examined by ion-exchange chromatography for possible peptidic precursors of penicillin. A sulfur-containing compound, present in both the mycelial extracts and the culture filtrates, was eluted at the location of the synthetic lld-tripeptide δ-(l-α-aminoadipyl)-l-cysteinyl-d-valine. Since this compound was also labeled when the cultures were incubated with dl-[6-14C]α-aminoadipic acid, l-[3,3′-3H]cystine, or dl-[1-14C]valine, its identity with the synthetic lld-tripeptide can be accepted. No δ-(l-α-aminoadipyl)-l-cysteine or lll-tripeptide were detected. The implications of these findings for tripeptide and penicillin biosynthesis are discussed.

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Selected References

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

  1. ARNSTEIN H. R., ARTMAN M., MORRIS D., TOMS E. J. Sulphur-containing amino acids and peptides in the mycelium of Penicillium chrysogenum. Biochem J. 1960 Aug;76:353–357. doi: 10.1042/bj0760353. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. ARNSTEIN H. R., HALLIDAY W. J. The biosynthesis of penicillin. 4. The synthesis of benzylpenicillin by washed mycelium of Penicillium chrysogenum. Biochem J. 1956 Oct;64(2):380–384. doi: 10.1042/bj0640380. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. ARNSTEIN H. R., MARGREITER H. The biosynthesis of penicillin. 7. Further experiments on the utilization of L-and D-valine and the effect of cystine and valine analogues on penicillin synthesis. Biochem J. 1958 Feb;68(2):339–348. doi: 10.1042/bj0680339. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. 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]
  5. Bauer K. Zur Biosynthese der Penicilline: Bildung von 5-(2-Aminoadipyl)-cysteinyl-valin in Extration von Penicillium chryogenum. Z Naturforsch B. 1970 Oct;25(10):1125–1129. [PubMed] [Google Scholar]
  6. COLE M., BATCHELOR F. R. Aminoadipylpenicillin in penicillin fermentations. Nature. 1963;198:383–384. doi: 10.1038/198383a0. [DOI] [PubMed] [Google Scholar]
  7. DEMAIN A. L. L-Valine: a precursor of cephalosporin C. Biochem Biophys Res Commun. 1963 Jan 18;10:45–48. doi: 10.1016/0006-291x(63)90265-1. [DOI] [PubMed] [Google Scholar]
  8. Demain A. L. Biochemistry of penicillin and cephalosporin fermentations. Lloydia. 1974 Jun;37(2):147–167. [PubMed] [Google Scholar]
  9. Frøshov Ø, Zimmer T. L., Laland S. G. The nature of the enzyme bound intermediates in gramicidin s biosynthesis. FEBS Lett. 1970 Mar 16;7(1):68–71. doi: 10.1016/0014-5793(70)80620-2. [DOI] [PubMed] [Google Scholar]
  10. HALLIDAY W. J., BRADFIELD B. E., SHAW M. K. The isolation of D-valine from Penicillium chrysogenum. Biochim Biophys Acta. 1960 Aug 12;42:377–378. doi: 10.1016/0006-3002(60)90813-1. [DOI] [PubMed] [Google Scholar]
  11. Kurahashi K., Yamada M., Mori K., Fujikawa K., Kambe M., Imae Y., Sato E., Takahashi H., Sakamoto Y. Biosynthesis of cyclic oligopeptide. Cold Spring Harb Symp Quant Biol. 1969;34:815–826. doi: 10.1101/sqb.1969.034.01.093. [DOI] [PubMed] [Google Scholar]
  12. Loder P. B., Abraham E. P. Isolation and nature of intracellular peptides from a cephalosporin C-producing Cephalosporium sp. Biochem J. 1971 Jul;123(3):471–476. doi: 10.1042/bj1230471. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. MACDONALD K. D., HUTCHINSON J. M., GILLETT W. A. ISOLATION OF AUXOTROPHS OF PENICILLIUM CHRYSOGENUM AND THEIR PENICILLIN YIELDS. J Gen Microbiol. 1963 Dec;33:365–374. doi: 10.1099/00221287-33-3-365. [DOI] [PubMed] [Google Scholar]
  14. NISHIMURA J. S., DODD E. A., MEISTER A. INTERMEDIATE FORMATION OF DIPEPTIDE-PHOSPHATE ANHYDRIDE IN ENZYMATIC TRIPEPTIDE SYNTHESIS. J Biol Chem. 1964 Aug;239:2553–2558. [PubMed] [Google Scholar]
  15. SNOKE J. E., BLOCH K. Formation and utilization of gamma-glutamylcysteine in glutathione synthesis. J Biol Chem. 1952 Nov;199(1):407–414. [PubMed] [Google Scholar]
  16. STEVENS C. M., INAMINE E., DE LONG C. W. The rates of incorporation of L-cystine and D- and L-valine in penicillin biosynthesis. J Biol Chem. 1956 Mar;219(1):405–409. [PubMed] [Google Scholar]
  17. STEVENS C. M., VOHRA P., DE LONG C. W. Utilization of valine in the biosynthesis of penicillins. J Biol Chem. 1954 Nov;211(1):297–300. [PubMed] [Google Scholar]
  18. 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]
  19. Vega A., Nunn P. B. A lithium buffer system for single-column amino acid analysis. Anal Biochem. 1969 Dec;32(3):446–453. doi: 10.1016/s0003-2697(69)80012-6. [DOI] [PubMed] [Google Scholar]
  20. Warren S. C., Newton G. G., Abraham E. P. The role of valine in the biosynthesis of penicillin N and cephalosporin C by a Cephalosporium sp. Biochem J. 1967 Jun;103(3):902–912. doi: 10.1042/bj1030902. [DOI] [PMC free article] [PubMed] [Google Scholar]
  21. Warren S. C., Newton G. G., Abraham E. P. Use of alpha-aminoadipic acid for the biosynthesis of penicillin N and cephalosporin C by a Cephalosporium sp. Biochem J. 1967 Jun;103(3):891–901. doi: 10.1042/bj1030891. [DOI] [PMC free article] [PubMed] [Google Scholar]

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