Bergofungin D, a peptaibol template for the introduction of chemical modifications, synthesis of analogs and comparative studies of their structures - Université de Montpellier
Article Dans Une Revue Journal of Peptide Science Année : 2024

Bergofungin D, a peptaibol template for the introduction of chemical modifications, synthesis of analogs and comparative studies of their structures

Résumé

Bergofungin D is a helical peptide of the peptaibol family consisting of 14 amino acids, six of which are the helix inducer aminoisobutyric acid (Aib). In the second third of the sequence, a hydroxyproline causes a bending of the helix and a disruption of the hydrogen bond network, and Aib7 is the only amino acid in this region involved in the hydrogen bond network. Therefore, modification of this residue can serve as a probe to monitor the effect of introducing amino acid substitutions on this more fragile helical turn. To validate this approach, we simplified the original bergofungin D by reducing the number of non‐classical amino acids, replacing the (R)‐isovaleric acid by its enantiomer or an Aib and the hydroxyproline with a proline, respectively, without affecting its secondary structure. Within the modified structure, we replaced Aib7‐Aib8 by its 1,2,3‐triazolodipeptide equivalent or Aib7 by a serine or a dehydrobutyrine. We have reported and analyzed five crystal structures, three of which are new, demonstrating the usefulness of the modified bergofungin D as a probe for monitoring the introduction of amino acid substitutions within a helical structure.

Domaines

Chimie
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Dates et versions

hal-04549901 , version 1 (17-04-2024)

Identifiants

Citer

Sanjit Das, Khoubaib Ben Haj Salah, Emmanuel Wenger, Baptiste Legrand, Claude Didierjean, et al.. Bergofungin D, a peptaibol template for the introduction of chemical modifications, synthesis of analogs and comparative studies of their structures. Journal of Peptide Science, 2024, ⟨10.1002/psc.3598⟩. ⟨hal-04549901⟩
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