Sequence diversity of the peptaibol antibiotic suzukacillin-A from the moldTrichoderma viride

Abstract

From the culture broth of the mold Trichoderma viride, strain 63 C-I, the polypeptide antibiotic suzukacillin (SZ) was isolated. A peptide mixture named SZ-A was obtained by crystallization from crude SZ. Individual peptides from SZ-A were isolated by semipreparative HPLC and sequences were determined by HPLC-ESI-MS. The data confirm a general sequence of SZ-A published previously and in addition establish the individual sequences of 15 acetylated eicosa peptides with C-terminal alcohols. The major peptide SZ-A4 (21% of all peptides) shows the sequence:Ac-Aib-Ala-Aib-Ala-Aib-Ala(6)-Gln-Aib-Lx(9)-Aib-Gly-Aib(12)-Aib-Pro-Vx(15)-Aib-Vx(17)-Gln-Gln-Fol. Amino acid exchanges of the peptaibol are located in position 6 (Ala/Aib), 9 (Vx/Lx), 12 (Aib/Lx), 17 (Aib/Vx) and possibly at position15 (Val/Iva) (uncommon abbreviations: Aib (alpha-aminoisobutyric acid); Iva (D-isovaline); Lx (L-leucine or L-isoleucine); Vx (L-valine or D-isovaline); Fol (L-phenylalaninol)).

Occurrence and characterization of peptaibols from Trichoderma citrinoviride, an endophytic fungus of cork oak, using electrospray ionization quadrupole time-of-flight mass spectrometry

“…12; Krause et al, 2006) Production of peptaibols by endophytic Trichoderma exchange of isobaric Val/Iva or Leu/Ile, we presume that they represent different dimeric combinations of the peptides. Thus, sequences 3a and 3b could be seen as the monomeric form of the heterodimer (peak 3 in the chromatogram) identifiable by a triply charged ion at m/z 1273.07.…”

“…Among the 28 identified structures, at least seven sequences are new. The others must correspond to the paracelsin, saturnisporin, trichocellin, longibrachin and suzukacillin types (Rebuffat et al, 1993;Wada et al, 1994;Pó csfalvi et al, 1997;Leclerc et al, 1998;Krause et al, 2006).…”

New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review

“…Thus, 15 individual 20-residue peptaibols, SZ-A1 -A9, -A10a/b, -A11a/b, and SZ-A12 -A13, were shown to be present in total. Despite the microheterogeneity, complete sequences of all SZ-A peptaibols and chirality of the individual amino acids have been determined by HPLC/MS n and GC/ EI-MS approaches [23]. In this context, the previously established presence of d-Iva [24] was confirmed.…”

Peptaibiomics: Towards a Myriad of Bioactive Peptides Containing Cα‐Dialkylamino Acids?

“…The N-terminus of these peptaibiotics is blocked by an decanoic acid residue, and the C-terminus is amidated by 1,2-diamino-4-methylpentane (DMAP) [183]. n and GC/EI-MS approaches [9]. In this context, the previously established presence of d-Iva [59] was confirmed.…”