title: Sequences of stilboflavin C: towards the peptaibiome of the filamentous fungus Stilbella (= Trichoderma) flavipes.
abstract: Filamentous fungi of the genus Stilbella are recognized as an abundant source of naturally occurring α-aminoisobutyric acid-containing peptides. The culture broth of Stilbella (Trichoderma) flavipes CBS 146.81 yielded a mixture of peptides named stilboflavins (SF), and these were isolated and separated by preparative TLC into groups named SF-A, SF-B, and SF-C. Although all three of these groups resolved as single spots on thin-layer chromatograms, HPLC analysis revealed that each of the groups represents very microheterogeneous mixtures of closely related peptides. Here, we report on the sequence analysis of SF-C peptides, formerly isolated by preparative TLC. HPLC coupled to QqTOF-ESI-HRMS provided the sequences of 10 16-residue peptides and five 19-residue peptides, all of which were N-terminally acetylated. In contrast to the previously described SF-A and SF-B peptaibols, SF-C peptaibols contain Ser-Alaol or Ser-Leuol, which are rarely found as C-termini, and repetitive Leu-Aib-Gly sequences, which have not been detected in peptaibols before. Taking the previously determined sequences of SF-A and SF-B into account, the entirety of peptides produced by S. flavipes (the 'peptaibiome') approaches or exceeds 100 non-ribosomally biosynthesized peptaibiotics. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.
authors.affiliation: Institute for Insect Biotechnology, Department of Applied Entomology, Interdisciplinary Research Center for BioSystems, Land Use and Nutrition (IFZ), Justus-Liebig-University of Giessen, Heinrich-Buff-Ring 26-32, 35392, Giessen, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Degenkolb
authors.affiliation: Department of Bioresources, Fraunhofer Institute for Molecular Biology and Applied Ecology, Winchester Strasse 2, 35394, Giessen, Germany.
authors.forename: Lutz
authors.initials: L
authors.lastname: Götze
authors.affiliation: Biochemistry and Molecular Biology OE 2, Institute of Chemistry, Technical University of Berlin, Franklinstrasse 29, 10587, Berlin, Germany.|Schillerstrasse 34, 10627, Berlin, Germany.
authors.forename: Hans
authors.initials: H
authors.lastname: von Döhren
authors.affiliation: Institute for Insect Biotechnology, Department of Applied Entomology, Interdisciplinary Research Center for BioSystems, Land Use and Nutrition (IFZ), Justus-Liebig-University of Giessen, Heinrich-Buff-Ring 26-32, 35392, Giessen, Germany.|Department of Bioresources, Fraunhofer Institute for Molecular Biology and Applied Ecology, Winchester Strasse 2, 35394, Giessen, Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Vilcinskas
authors.affiliation: Institute for Insect Biotechnology, Department of Applied Entomology, Interdisciplinary Research Center for BioSystems, Land Use and Nutrition (IFZ), Justus-Liebig-University of Giessen, Heinrich-Buff-Ring 26-32, 35392, Giessen, Germany.
authors.forename: Hans
authors.initials: H
authors.lastname: Brückner
mesh_terms: D000107:Acetylation; D000595:Amino Acid Sequence; D000621:Aminoisobutyric Acids / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D003470:Culture Media / Q000737:chemistry; D005656:Fungal Proteins / Q000737:chemistry* / Q000145:classification / Q000302:isolation & purification; D054848:Peptaibols / Q000737:chemistry* / Q000145:classification / Q000302:isolation & purification; D017433:Protein Structure, Secondary; D020543:Proteome / Q000737:chemistry* / Q000145:classification / Q000302:isolation & purification; D020539:Sequence Analysis, Protein; D014242:Trichoderma / Q000737:chemistry* / Q000502:physiology
chemical_list: D000621:Aminoisobutyric Acids; D003470:Culture Media; D005656:Fungal Proteins; D054848:Peptaibols; D020543:Proteome; C100049:2-aminoisobutyric acid
keywords: Chirasil-l-Val; electrospray mass spectrometry; gas chromatography-selected ion mass spectrometry, Stilbella, Trichoderma; non-ribosomal peptide synthesis; peptaibiotics; peptaibols; α-aminoisobutyric acid (Aib), polypeptide antibiotics