𝔖 Bobbio Scriptorium
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Synthesis and Conformational Analysis of Efrapeptins

✍ Scribed by Dr. Sven Weigelt; Dr. Thomas Huber; Frank Hofmann; Dr. Micha Jost; Markus Ritzefeld; Prof. Dr. Burkhard Luy; Dr. Christoph Freudenberger; Prof. Dr. Zsuzsanna Majer; Prof. Dr. Elemér Vass; Dr. Jörg-Christian Greie; Dr. Lavinia Panella; Dr. Bernard Kaptein; Dr. Quirinus B. Broxterman; Prof. Dr. Horst Kessler; Prof. Dr. Karlheinz Altendorf; Prof. Dr. Miklós Hollósi; Prof. Dr. Norbert Sewald

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
840 KB
Volume
18
Category
Article
ISSN
0947-6539

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✦ Synopsis

Abstract

The efrapeptin family of peptide antibiotics produced by the fungus Tolypocladium niveum, and the neo‐efrapeptins from the fungus __Geotrichum candidum__are inhibitors of F~1~‐ATPase with promising antitumor, antimalaria, and insecticidal activity. They are rich in C^α^‐dialkyl amino acids (Aib, Iva, Acc) and contain one β‐alanine and several pipecolic acid residues. The C‐terminus bears an unusual heterocyclic cationic cap. The efrapeptins C–G and three analogues of efrapeptin C were synthesized using α‐azido carboxylic acids as masked amino acid derivatives. All compounds display inhibitory activity toward F~1~‐ATPase. The conformation in solution of the peptides was investigated with electronic CD spectroscopy, FT‐IR spectroscopy, and VCD spectroscopy. All efrapeptins and most efrapeptin analogues were shown to adopt helical conformations in solution. In the case of efrapeptin C, VCD spectra proved that a 3~10~‐helix prevails. In addition, efrapeptin C was conformationally studied in detail with NMR and molecular modeling. Besides NOE distance restraints, residual dipolar couplings (RDC) observed upon partial alignment with stretched PDMS gels were used for the conformational analysis and confirmed the 3~10~‐helical conformation.

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