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Claudio Toniolo and Hans Brückner (Eds.)

Fungal Peptides Containing alpha-Dialkyl alpha-Amino Acids






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ISBN-10: 3-906390-52-7
ISBN-13: 978-3-906390-52-9
702 pages


This book provides an excellent overview on the status of contemporary studies of peptaibiotics, covering aspects ranging from the search for novel bioactive compounds and their biosynthetic aspects to the total chemical synthesis and exploitation of X-ray diffraction and various spectroscopic techniques, to considerations of their membrane-modifying properties, including mechanisms of transmembrane channel formation through peptide self-association.

The articles compiled in this book represent also a legitimation of the long-standing interest of the Editors and their co-workers and collaborators in the field of natural and synthetic Aib-rich peptides, and are an appropriate tribute to the pioneers of the research in peptaibiotics.


Peptaibiomics: Towards a Myriad of Bioactive Peptides Containing C(alpha)-Dialkylamino Acids?
The History of Alamethicin: A Review of the Most Extensively Studied Peptaibol
New Sequences, Constituents, and Producers of Peptaibiotics
Aib and Iva in the Biosphere: Neither Rare nor Necessarily Extraterrestrial

Peptaibiomics: Microheterogeneity, Dynamics, and Sequences of Trichobrachins, Peptaibiotics from Trichoderma parceramosum BISSETT (T. longibrachiatum RIFAI)
The Production and Characterisation of Trichotoxin Peptaibols, by Trichoderma asperellum
Peptaibol Production by Sepedonium Strains Parasitizing Boletales
Peptaibols: Stable Markers of Fungal Development in the Marine Environment
Peptaibiomics: Screening for Polypeptide Antibiotics (Peptaibiotics) from Plant-Protective Trichoderma Species

Total Synthesis in Solution and Conformational Analysis of the Peptaibol Cervinin and Selected Analogues
The "Azirine/Oxazolone Method" in Peptaibol Synthesis: Preparation of a Derivative of Trichotoxin A-50 (G)
Synthesis, and Structural and Biological Studies of Efrapeptin C Analogues
Total Syntheses in Solution of TOAC-Labelled Alamethicin F50/5 Analogues
alpha,alpha'-Disubstituted Amino Acids with Silylated Side Chains as Lipophilic Building Blocks for the Synthesis of Peptaibol Analogues
Synthesis and Conformational Analysis of Pentapeptides Containing Enantiomerically Pure 2,2-Disubstituted Glycines
The First Total Synthesis of the Peptaibol Hypomurocin A1 and Its Conformation Analysis: an Application of the "Azirine/Oxazolone Method"
Studies on the Selective Trifluoroacetolytic Scission of Native Peptaibols and Model Peptides Using HPLC and ESI-CID-MS

Ligand-Induced Extramembrane Conformation Switch Controlling Alamethicin Assembly and the Channel Current
Channel-Forming Activity of Alamethicin: Effects of Covalent Tethering
Multinuclear Solid-State-NMR and FT-IR-Absorption Investigations on Lipid/Trichogin Bilayers
Main-Chain Length Control of Conformation, Membrane Activity, and Antibiotic Properties of Lipopeptaibol Sequential Analogues
Antiamoebin I in Methanol Solution: Rapid Exchange between Right-Handed and Left-Handed 310-Helical Conformations
Solvent Effects on the Secondary Structure of the Membrane-Active Zervamicin Determined by PELDOR Spectroscopy
Conformational Analysis of TOAC-Labelled Alamethicin F50/5 Analogues
Solvent Dependence of the Rotational Diffusion of TOAC-Spin-Labeled Alamethicin
Supramolecular Structure of Self-Assembling Alamethicin Analog Studied by ESR and PELDOR
Alamethicin Interaction with Lipid Membranes: A Spectroscopic Study on Synthetic Analogues
Conformational Effects on the Electron-Transfer Efficiency in Peptide Foldamers Based on alpha,alpha-Disubstituted Glycyl Residues
Aib Residues in Peptaibiotics and Synthetic Sequences: Analysis of Nonhelical Conformations
Pore-Forming Properties of Alamethicin F50/5 Inserted in a Biological Membrane
Membrane Permeabilization of a Mammalian Neuroendocrine Cell Type (PC12) by the Channel-Forming Peptides Zervamicin, Alamethicin, and Gramicidin

Facts and Challenges in the Understanding of the Biosynthesis of Peptaibols by Trichoderma
Recent Advances and Future Prospects in Peptaibiotics, Hydrophobin, and Mycotoxin Research, and Their Importance for Chemotaxonomy of Trichoderma and Hypocrea
The Peptaibol Alamethicin Induces an rRNA-Cleavage-Associated Death in Arabidopsis thaliana
Neuroleptic Properties of the Ion-Channel-Forming Peptaibol Zervamicin: Locomotor Activity and Behavioral Effects
Enzymatic Reaction in a Vesicular Microreactor: Peptaibol-Facilitated Substrate Transport

Natural Cyclopeptaibiotics and Related Cyclic Tetrapeptides
Synthetic Antimicrobial Peptides as Agricultural Pesticides for Plant-Disease Control
Synthetic, Biologically Active Amphiphilic Peptides
Peptaibiotics and Peptaibols: An Alternative to Classical Antibiotics?

Genus and Species Index
Subject Index