Intramolecularly stapled amphipathic peptides via a boron–sugar interaction

Monika Kijewska; Angelika Czerwińska; Samah Al-Harthi; Grzegorz Wołczański; Mateusz Waliczek; Abdul-Hamid Emwas; Mariusz Jaremko; Łukasz Jaremko; Piotr Stefanowicz; Zbigniew Szewczuk

doi:10.1039/D0CC02603D

Intramolecularly stapled amphipathic peptides via a boron–sugar interaction†

Monika Kijewska,

*^a Angelika Czerwińska,^a Samah Al-Harthi,

^b Grzegorz Wołczański,^a Mateusz Waliczek,^a Abdul-Hamid Emwas,^b Mariusz Jaremko,

^b Łukasz Jaremko,^b Piotr Stefanowicz

^a and Zbigniew Szewczuk

^a

Author affiliations

* Corresponding authors

^a Faculty of Chemistry, University of Wrocław, Joliot-Curie 14, 50-383 Wrocław, Poland
E-mail: monika.kijewska@chem.uni.wroc.pl

^b King Abdullah University of Science and Technology (KAUST), Biological and Environmental Sciences & Engineering Division (BESE), Thuwal, Saudi Arabia

Abstract

Amadori products (deoxyfructosyllysine derivatives) that can selectively interact with phenylboronic acids and borate ions were synthesized. The intramolecular interactions between the fructosyl moiety and phenylboronic acid incorporated into various positions of the peptide chain were investigated using high-resolution mass spectrometry (HR–MS), circular dichroism (CD), and nuclear magnetic resonance (NMR).

Chemical Communications

Intramolecularly stapled amphipathic peptides via a boron–sugar interaction†

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Intramolecularly stapled amphipathic peptides via a boron–sugar interaction

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