A temperature-driven, reversible helical handedness inversion in peptaibol analogs tuned by the C-terminal capping moiety.

08:00 EDT 16th May 2019 | BioPortfolio

Summary of "A temperature-driven, reversible helical handedness inversion in peptaibol analogs tuned by the C-terminal capping moiety."

Trichogin is a natural peptide endowed with antimicrobial and antitumor activity. A member of the peptaibol family, trichogin possesses a C-terminal aminoalcohol. In the past, we substituted that moiety with a methyl ester for synthetic purposes and realized that this apparently slight modification causes great changes in the peptide bioactivity. Aiming at understanding the reasons behind such observations, we performed a detailed spectroscopic study on a number of trichogin analogs. In the present manuscript, we compare the data obtained from synchrotron radiation circular dichroism, NMR and fluorescence spectroscopy in organic solvents at cryogenic temperatures with those independently acquired by electron paramagnetic resonance spectroscopy at 80K. We reveal unambiguously the presence of a reversible, temperature-driven screw-sense interconversion from right-handed to left-handed helix that is determined by the C-terminal capping moiety. Our data demonstrate for the first time the key role of a C-terminal methyl ester in promoting peptide screw-sense inversion.


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This article was published in the following journal.

Name: Chembiochem : a European journal of chemical biology
ISSN: 1439-7633


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