Issue 50, 2016

Electronic interactions of i, i + 1 dithioamides: increased fluorescence quenching and evidence for n-to-π* interactions

Abstract

Thioamide residues can be effective, minimally-perturbing fluorescence quenching probes for studying protein folding and proteolysis. In order to increase the level of quenching, we have here explored the use of adjacent dithioamides. We have found that they are more effective fluorescence quenchers, as expected, but we have also observed unexpected changes in the thioamide absorption spectra that may arise from n-to-π* interactions of the thiocarbonyls. We have made use of the increased quenching to improve the fluorescence turn-on of thioamide protease sensors.

Graphical abstract: Electronic interactions of i, i + 1 dithioamides: increased fluorescence quenching and evidence for n-to-π* interactions

  • This article is part of the themed collection: Foldamers

Supplementary files

Article information

Article type
Communication
Submitted
06 jan 2016
Accepted
23 máj 2016
First published
27 máj 2016

Chem. Commun., 2016,52, 7798-7801

Author version available

Electronic interactions of i, i + 1 dithioamides: increased fluorescence quenching and evidence for n-to-π* interactions

Y. Huang, J. J. Ferrie, X. Chen, Y. Zhang, D. M. Szantai-Kis, D. M. Chenoweth and E. J. Petersson, Chem. Commun., 2016, 52, 7798 DOI: 10.1039/C6CC00105J

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