Sequences of alamethicins F30 and F50 reconsidered and reconciled

  title={Sequences of alamethicins F30 and F50 reconsidered and reconciled},
  author={Jochen Kirschbaum and Corina Krause and Ruth K Winzheimer and Hans Br{\"u}ckner},
  journal={Journal of Peptide Science},
From the culture broth of the mould Trichoderma viride, strain NRRL 3199, a microheterogeneous mixture of the membrane active 20‐residue peptaibol alamethicin (ALM) could be isolated. ALMs were isolated by XAD‐2 column chromatography and separated by silica gel chromatography and trichloromethane/MeOH gradient elution into an acidic and neutral group of peptides, named ALM F30 and ALM F50, respectively, according to their 100 Rf on TLC. Peptides ALM F50 were separated by semi‐preparative and… 
Peptaibiomics: Microheterogeneity, Dynamics, and Sequences of Trichobrachins, Peptaibiotics from Trichoderma parceramosum Bissett (T. longibrachiatum Rifai)
Monitoring production and degradation of peptaibiotics in a pilot experiment revealed that the biosynthesis of TB II and TB III peptides starts two days after the beginning of fermentation, which unequivocally demonstrates that those two 18‐residue TB I and TB II peptides with the free carboxy terminus result from enzymatic C‐terminal degradation of the 20‐resido peptides.
Studies on the Selective Trifluoroacetolytic Scission of Native Peptaibols and Model Peptides Using HPLC and ESI‐CID‐MS
From the conspicuous concordance of the formation and abundance of regular series of trifluoroacetolytic fragments and of positive ions of the b‐series in CID‐MS, the generation of intermediate oxazolonium ions in both gas and liquid phase is concluded.
Detection of new amino acid sequences of alamethicins F30 by nonaqueous capillary electrophoresis–mass spectrometry
The microheterogeneous alamethicin F30 (ALM F30) isolated from the fermentation of Trichoderma viride strain NRRL 3199 was analyzed by nonaqueous capillary electrophoresis coupled to electrospray
Total synthesis in solution of alamethicin F50/5 by an easily tunable segment condensation approach
This tunable segment condensation approach will pave the way for an easy synthesis of alamethicin analogues bearing amino acid residues with desired side‐chain probes even at the N‐terminus and in internal positions of the sequence.
Profiling of trichorzianines in culture samples of Trichoderma atroviride by liquid chromatography/tandem mass spectrometry.
The profiling method was successfully applied to culture samples of T. atroviride P1 wild-type and two deletion mutants showing different trichorzianine expression patterns characteristic for the investigated fungal strains.
Analysis of the lipophilic peptaibol alamethicin by nonaqueous capillary electrophoresis‐electrospray ionization‐mass spectrometry
The microheterogeneous peptaibol alamethicin F30 isolated from the culture broth of Trichoderma viride was analyzed by nonaqueous CE‐electrospray‐MS using an IT and a TOF mass analyzer and proper selection of the precursor ions allowed the unequivocal analysis of the components.
Trichoderma brevicompactum complex: Rich source of novel and recurrent plant-protective polypeptide antibiotics (peptaibiotics).
Three strains of Trichoderma brevicompactum and another four that are closely related to that species were analyzed for the formation of polypeptide antibiotics (peptaibiotics) by LC/ESI-MS(n).
New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review
To introduce fungal species hitherto unknown as producers of peptaibiotics, the relevant literature is reviewed and ecophysiological and taxonomic aspects of the producing fungi are discussed.
Sequence diversity of the peptaibol antibiotic suzukacillin‐A from the mold Trichoderma viride
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
New 19-Residue Peptaibols from Trichoderma Clade Viride
Trichoderma koningiopsis and T. gamsii belong to clade Viride of Trichoderma, the largest and most diverse group of this genus. They produce a wide range of bioactive secondary metabolites, including


Structures of trichovirins II, peptaibol antibiotics from the mold Trichoderma viride NRRL 5243
From the culture broth of the mold Trichoderma viride NRRL 5243 a mixture of polypeptides, named trichovirins (TV), could be isolated and purified by chromatography on XAD‐2 adsorber resin and
Sequences of polypeptide antibiotics stilboflavins, natural peptaibol libraries of the mold Stilbella flavipes
  • A. Jaworski, H. Brückner
  • Chemistry, Biology
    Journal of peptide science : an official publication of the European Peptide Society
  • 2001
From the culture broths of the mold Stilbella flavipes CBS 146.81, a mixture of polypeptides could be isolated by adsorption on XAD polystyrene resin and purified by Sephadex LH‐20 chromatography.
Die hämolytischen Eigenschaften der membranmodifizierenden Peptidantibiotika Alamethicin, Suzukacillin und Trichotoxin
A detailed study of the hemolytic action with variations of concentration, temperature and incubation time revealed characteristic differences in the mode of hemolysis between the peptide antibiotics, which can be correlated with structural differences between these natural analogs.
Total Synthesis of the α‐Helical Eicosapeptide Antibiotic Alamethicin
The voltage-dependent membrane pore-forming polypeptide antibiotic alamethicin F 30 (Ac-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib-Val-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib-Glu-Gln-Phl, 1) was synthesized by segment
Facilitated synthesis of peptaibols: Alamethicin via enzymatic segment condensation
A combined chemical‐enzymatic approach was used to facilitate the total synthesis of the 20‐residue peptaibol, alamethicin, and the papain‐catalyzed coupling proceeded readily and selectively using a C‐terminal segment having a free γ‐carboxyl group at this position.
The primary structure of alamethicin.
Alamethicin, an antibiotic that can transport cations and induce action potentials in synthetic membranes, is shown to be a cyclic peptide with 18 residues including 7-alpha-aminoisobutyric acid
Synthesis of a 19-residue peptide with alamethicin-like activity.
It is established that a cyclic structure is not a necessary condition for a peptide to induce voltage-dependent conductances in membranes and that ALA-o possesses all the structural elements required for such an activity.
Conformational changes of alamethicin induced by solvent and temperature. A 13C-NMR and circular-dichroism study.
13C nuclear magnetic resonance (NMR) and circular dichroism (CD) have been used for studies on the conformation of alamethicin. The 13C NMR spectrum is assigned with the aid of signals of synthetic
Chemical nature and sequence of alamethicin.
The new formula of pure alamethicin is confirmed by a comparison between pure chemical compounds and the products of partial hydrolysis.