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A temperature‐driven, reversible helical handedness inversion in peptaibol analogs tuned by the C‐terminal capping moiety
Authors:
Marta
De Zotti
(University of Padova)
,
Victoria N.
Syryamina
(Institute of Chemical Kinetics and Combustion, RAS Novosibirsk; Novosibirsk State University)
,
Rohanah
Hussain
(Diamond Light Source)
,
Edoardo
Longo
(Free University of Bozen-Bolzano)
,
Giuliano
Siligardi
(Diamond Light Source)
,
Sergei A.
Dzuba
(Institute of Chemical Kinetics and Combustion, RAS Novosibirsk)
,
Lorenzo
Stella
(University of Rome Tor Vergata)
,
Fernando
Formaggio
(University of Padova)
Co-authored by industrial partner:
No
Type:
Journal Paper
Journal:
Chembiochem
State:
Published (Approved)
Published:
May 2019
Diamond Proposal Number(s):
13463
,
11528
,
14298
Abstract: 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.
Journal Keywords: antimicrobial peptide; conformational transition; C-terminal methyl ester; screwsense switch; synchrotron radiation circular dichroism
Subject Areas:
Biology and Bio-materials,
Chemistry
Instruments:
B23-Circular Dichroism