Structures of trichovirins II, peptaibol antibiotics from the mold Trichoderma viride NRRL 5243

Journal of Peptide Science

Volumn 5, Issue 8, 1999, Pages 341-351

  Jaworski, Andreas ^a   Kirschbaum, Jochen ^a   Brückner, Hans ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

aminoisobutyric acid; Electrospray ionization mass spectrometry; Gas chromatography mass spectrometry; Isovaline; Peptide antibiotics; Sequence analysis; Trichotoxin

Indexed keywords

2 AMINO 2 METHYLPROPIONIC ACID; CHLOROFORM; FLUOROCARBON; LEUCINE; METHANOL; PEPTAIBOL; POLYPEPTIDE; RESIN; SEPHADEX; SILICA GEL; TRICHOVIRIN; UNCLASSIFIED DRUG;

ACETYLATION; AMINO ACID SEQUENCE; AMINO TERMINAL SEQUENCE; ARTICLE; BACTERICIDAL ACTIVITY; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; FUNGUS CULTURE; GAS CHROMATOGRAPHY; GEL CHROMATOGRAPHY; HEMOLYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTEIN ISOLATION; TANDEM MASS SPECTROMETRY; TRICHODERMA VIRIDE;

AMINO ACID SEQUENCE; ANIMALS; ANTI-BACTERIAL AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HEMOLYSIS; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN CONFORMATION; SEQUENCE HOMOLOGY, AMINO ACID; SHEEP; TRICHODERMA;

FUNGI; TRICHODERMA VIRIDE; TRICHOTOXIN;

EID: 0032767307     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1387(199908)5:8<341::AID-PSC204>3.0.CO;2-0     Document Type: Article

References (32)

1. Hou CT, Ciegler A, Hesseltine CW. New mycotoxin, trichotoxin A, from Trichoderma viride isolated from southern leaf blight-infected corn. Appl Microbiol 1972; 23: 183-185.
2. Irmscher G, Bovermann G, Boheim G, Jung G. Trichotoxin A-40, a new membrane-exciting peptide. Part A. Isolation, characterization and conformation. Biochim Biophys Acta 1978; 507: 470-484.
3. Brückner H, König WA, Aydin M, Jung G. Trichotoxin A 40. Purification by counter-current distribution and sequencing of isolated fragments. Biochim Biophys Acta 1985; 827: 51-62.
4. Przybylski M, Dietrich I, Manz I, Brückner H. Elucidation of structure and microheterogeneity of the polypeptide antibiotics paracelsin and trichotoxin A-50 by fast atom bombardment mass spectrometry in combination with selective in situ hydrolysis. Biomed Mass Spectrom 1984; 11: 569-582.
5. Pandey RC, Meng H, Cook JC, Rinehart KL. Structure of antiamoebin I from high resolution field desorption and gas chromatographic mass spectrometry studies. J Am Chem Soc 1977; 99: 5203-5205.
6. Boheim G, Irmscher G, Jung G. Trichotoxin A-40, a new membrane-exciting peptide. Part B. Voltage-dependent pore formation in bilayer lipid membranes and comparison with other alamethicin analogues. Biochim Biophys Acta 1978; 507: 485-506.
7. Sansom MSP. Alamethicin and related peptaibols-model ion channels. Eur Biophys J 1993; 22: 105-124.
8. Duclohier H, Snook CF, Wallace BA. Antiamoebin can function as a carrier or as pore-forming peptaibol. Biochim Biophys Acta 1998; 1414: 255-260.
9. Fox RO, Richards FM. A voltage-gated ion channel model inferred from the crystal structure of alamethicin at 1.5-Å resolution. Nature 1982; 300: 325-330.
10. Aubry A, Bayeul D, Brückner H, Schiemann N, Benedetti E. The crystal state conformation of Aib-rich segments of peptaibol antibiotics. J Peptide Sci 1998; 4: 502-510.
11. Schirmböck M, Lorito M, Wang Y, Hayes C, Arisan-Atac I, Scala F, Harman G, Kubicek C. Parallel formation and synergism of hydrolytic enzymes and peptaibol antibiotics, molecular mechanisms involved in the antagonistic action of Trichoderma harzianum against phytopathogenic fungi. Appl Environ Microbiol 1994; 60: 4364-4370.
12. Solfrizzo D, Altomare C, Visconti A, Bottalico A, Perrone G. Detection of peptaibols and their hydrolysis products in cultures of Trichoderma species. Natural Toxins 1994; 2: 360-365.
13. Brückner H, Maisch J, Reinecke C, Kimonyo A. Use of α-aminoisobutyric acid and isovaline as marker amino acids for the detection of fungal polypeptide antibiotics. Screening of Hypocrea. Amino Acids 1991; 1: 251-257.
14. st European Peptide Symposium. E Giralt, D Andreu, Eds, p. 347-349, ESCOM, Leiden, The Netherlands, 1991.
15. Mat̂ha V, Jegorov A, Kiess M, Brückner H. Morphological alterations accompanying the effect of peptaibiotics, α-aminoisobutyric acid-rich secondary metabolites of filamentous fungi, on Culex pipiens larvae. Tissue Cell 1992; 24: 559-564.
16. Auvin-Guette C, Rebuffat S, Prigent Y, Bodo B. Trichogin A IV, an 11-residue lipopeptaibol from Trichoderma longibrachiatum. J Am Chem Soc 1992; 114: 2170-2174.
17. Gräfe U, Ihn W, Ritzau M, Schade W, Stengel C, Schlegel B, Fleck WF, Künkel W, Härtl A, Gutsche W. Helioferins; novel antifungal lipopeptides from Mycogone rosea: screening, isolation, structures and biological properties. J Antibiotics 1995; 48: 126-133.
18. Kieß M, Brückner H. Trichovirin: fermentation, isolation and sequence determination of a polypeptide antibiotic, in DECHEMA Biotechnology Conferences, 4B, p. 1155-1158, VCH, Weinheim, 1990.
19. Brückner H, Kripp T, Kieß M. Polypeptide antibiotics trichovirin and trichobrachin: sequence determination and total synthesis, in Chemistry of Peptides and Proteins, Vol. 5/6, Part A. D Brandenburg, V Ivanov, W Voelter, Eds, p. 357-373, DWI Reports TH Aachen, Verlag Mainz, Aachen, 1993.
20. Greenstein JP, Winitz M. Chemistry of the Amino Acids, Vol. 3, Chapter 47. Wiley, New York, 1961.
21. Prox A, Schmidt J, Ottenheym H. Die Struktur des Antamanids. Liebigs Ann Chem 1969; 722:179-196.
22. Bosch R, Brückner H, Jung G, Winter W. (-)-Isovaline: confirmation of its D-(= R)-configuration by x-ray analysis of its N-chloroacetyl derivate. Tetrahedron 1982; 38: 3579-3583.
23. Monde T, Kamiusuki T, Kuroda T, Mikumo K, Ohkawa T, Fukube H. High-performance liquid chromatographic separation of phenols on a fluorocarbon-bonded silica gel column. J Chromatogr A 1996; 722: 273-280.
24. Becker D, Kieß M, Bruckner H. Structures of peptaibol antibiotics hypomurocin A and B from the ascomycetous fungus Hypocrea muroiana Hino et Katsumoto. Liebigs Ann/Recueil 1997: 767-772.
25. Goulard C, Hlimi S, Rebuffat S, Bodo B. Trichorzins HA and MA, antibiotic peptides from Trichoderma harzianum. I. Fermentation, isolation and biological properties. J Antibiotics 1995; 48:1248-1253.
26. Matsuura K, Shima T, Takaishi Y, Nagaoka Y, Fujita T. Fungal metabolites XV. Primary structures of antibiotic peptides, hypelcins B-I, B-II, B-III, B-IV and B-V, from Hypocrea peltata. Application of electrospray mass spectrometry and electrospray mass spectrometry/mass spectrometry. Chem Pharm Bull 1994; 42: 1063-1069.
27. Rebuffat S, Goulard C, Bodo B. Antibiotic peptides from Trichoderma harzianum: harzianins HC, proline-rich 14-residue peptaibols. J Chem Soc Perkin Trans I 1995: 1849-1855.
28. Auvin-Guette C, Rebuffat S, Vuidepot I, Massias M, Bodo B. Structural elucidation of trikoningins KA and KB, peptaibols from Trichoderma koningii. J Chem Soc Perkin Trans I 1993: 249-255.
29. Iida A, Sanekata M, Fujita T, Tanaka H, Enoki A, Fuse G, Kanai M, Rudewicz PJ, Tachikawa E. Fungal metabolites XVI. Structures of new peptaibols, trichokindins I-VII, from the fungus Trichoderma harzianum. Chem Pharm Bull 1994; 42: 1070-1075.
30. Iida A, Sanekata M, Wada SI, Fujita T, Tanaka H, Enoki A, Fuse G, Kanai M, Asami K. Fungal metabolites. XVIII. New membrane modifying peptides, trichorozins I-IV, from the fungus Trichoderma harzianum. Chem Pharm Bull 1995; 43: 392-397.
31. Fujita T, Wada SI, Iida A, Nishimura T, Kanai M, Toyama N. Fungal metabolites. XIII. Isolation and structural elucidation of new peptaibols, trichodecenins-I and -II, from Trichoderma viride. Chem Pharm Bull 1994; 42: 489-494.
32. Biemann K. Mass spectrometry of peptides and proteins. Annu Rev Biochem 1992; 61: 977-1010.