Skip to main content
Log in

Use ofα-aminoisobutyric acid and isovaline as marker amino acids for the detection of fungal polypeptide antibiotics. Screening ofHypocrea

  • Published:
Amino Acids Aims and scope Submit manuscript

Summary

Filamentous fungi of the genusHypocrea were grown on malt extract/peptone agar, the mycelia were extracted with dichloromethane/methanol, and the extracts were totally hydrolyzed with 6 N HCl (110°C, 24 h). The amino acids (AA) released from peptides were converted into theirN(O)-pen-tafluoropropionyl 1-propyl esters and investigated by gas chromatography and gas chromatography/mass spectrometry for the presence of the nonprotein AAα-aminoisobutyric acid (Aib) and its homologue isovaline (Iva). In particular Aib served as specific marker compound for a particular group of fungal peptides named peptaibiotics,i.e. peptides containing Aib and having antibiotic activities. Screening of 24 species ofHypocrea revealed that the majority was capable of producing peptaibiotics. The reliability of the screening procedure was shown with the isolation of peptaibiotics fromHypocrea muroiana andHypocrea nigricans. These findings extend the list of genera of fungi already known to produce Aib-containing peptides and also establish that Aib and Iva are fairly common in the biosphere.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Boheim G, Hanke W, Jung G (1983) Biophys Struct Mech 9: 181–191

    Google Scholar 

  • Brückner H, Nicholson GJ, Jung G, Kruse K, König WA (1980) Chromatographia 13: 209–214

    Google Scholar 

  • Brückner H, Graf H, Bokel M (1984) Experientia 40: 1189–1197

    Google Scholar 

  • Brückner H, Wunsch P, Kussin C (1989a) In: Aubry A, Marraud M, Vitoux B (eds) Second forum on peptides. Colloque INSERM, vol 174. John Libbey Eurotext, London, pp 103–106

    Google Scholar 

  • Brückner H, Kripp T, Kieß M (1991) In: Giralt E, Andreu D (eds) Peptides 1990. Proceedings of the twenty-first european peptide symposium, Platja d'Aro, Spain, 1990. Escom Science, Leiden, pp 347–349

    Google Scholar 

  • Brückner H, Langer M (1991) J Chromatogr 542: 161–172

    Google Scholar 

  • Bullough DA, Jackson CGH, Henderson PJF, Cottee FJ, Beechey RB, Linnett PE (1982) Biochem Int 4: 543–549

    Google Scholar 

  • Dennis C, Webster J (1971) Trans Br Mycol Soc 57: 25–39

    Google Scholar 

  • Fujita T, Takaishi Y, Matsuura, K, Takeda Y, Yoshioka Y, Brückner H (1984) Chem Pharm Bull 32: 2870–2873

    Google Scholar 

  • Gessmann R, Brueckner H, Kokkinidis M (1991) Biochem Biophys Res Comm 174: 878–884

    Google Scholar 

  • Hummel R-P, Toniolo C, Jung G (1987) Angew Chem 99: 1180–1182; Angew Chem Int Ed Engl 26: 1150–1152

    Google Scholar 

  • Jung G, Brückner H, Schmitt H (1981) In: Voelter W, Weitzel G (eds) Structure and activity of natural peptides. Proceedings Herbsttagung Gesellschaft Biologische Chemie, Tübingen, 1980. de Gruyter, Berlin, pp 75–114

    Google Scholar 

  • Karle IL, Flippen-Anderson JL, Uma K, Balaram P (1988) Int J Peptide Protein Res 32: 536–543

    Google Scholar 

  • Marshall GR, Clark JD, Dunbar JB, Smith GD, Zabrocki J, Redlinski AS, Leplawy MT (1988) Int J Peptide Protein Res 32: 544–555

    Google Scholar 

  • Moore LR (1969) In: Eglinton G, Murphy MTJ (eds) Organic geochemistry. Springer, Berlin Heidelberg New York, pp 265–303, and references cited therein

    Google Scholar 

  • Pandey RC, Cook JC, Rinehart KL (1977) J Am Chem Soc 99: 8469–8483

    Google Scholar 

  • Przybylski M, Dietrich I, Manz I, Brückner H (1984) Biomed Mass Spectrom 11: 569–582

    Google Scholar 

  • Rebuffat S, El Hajji M, Henning P, Davoust D, Bodo B (1989) Int J Peptide Protein Res 34: 200–210

    Google Scholar 

  • Toniolo C, Benedetti E (1988) ISI Atlas of science: Biochemistry 1: 225–230

    Google Scholar 

  • Zhao M, Bada, JL (1989) Nature 339: 463–465

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Brückner, H., Maisch, J., Reinecke, C. et al. Use ofα-aminoisobutyric acid and isovaline as marker amino acids for the detection of fungal polypeptide antibiotics. Screening ofHypocrea . Amino Acids 1, 251–257 (1991). https://doi.org/10.1007/BF00806923

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00806923

Keywords

Navigation