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Synthesis, and Structural and Biological Studies of Efrapeptin C Analogues

✍ Scribed by Micha Jost; Sven Weigelt; Thomas Huber; Zsuzsanna Majer; Jörg-Christian Greie; Karlheinz Altendorf; Norbert Sewald

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
296 KB
Volume
4
Category
Article
ISSN
1612-1872

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✦ Synopsis

Abstract

A series of analogues of efrapeptin C (1), with variations in the central tripeptide epitope (positions 6–8), were prepared by a combination of solid‐ and solution‐phase peptide syntheses. The conformations of the modified compounds 2–6 were investigated by circular‐dichroism (CD) spectroscopy to differentiate between 3~10~‐ and α‐helical secondary structures. The inhibitory activities of the new compounds towards F~1~‐ATPase from E. coli were determined. The modified congeners 3–5 were less active by one order of magnitude compared to 1 (K~i~ 10 μM), and 6 was completely inactive. Our experiments demonstrate that the flexible, central tripeptide epitope, comprising positions 6–8 in 1, is crucial for molecular recognition, even slight sequence modifications being hardly tolerated.

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