Salt-induced adaptation of a dynamic combinatorial library of pseudopeptidic macrocycles: unraveling the electrostatic effects in mixed aqueous media

Chemistry : a European Journal
Joan AtcherIgnacio Alfonso

Abstract

Dynamic combinatorial libraries are powerful systems for studying adaptive behaviors and relationships, as models of more complex molecular networks. With this aim, we set up a chemically diverse dynamic library of pseudopeptidic macrocycles containing amino-acid side chains with differently charged residues (negative, positive, and neutral). The responsive ability of this complex library upon the increase of the ionic strength has been thoroughly studied. The families of the macrocyclic members concentrating charges of the same sign showed a large increase in its proportion as the ionic strength increases, whereas those with residues of opposite charges showed the reverse behavior. This observation suggested an electrostatic shielding effect of the salt within the library of macrocycles. The top-down deconvolution of the library allowed us to obtain the fundamental thermodynamic information connecting the library members (exchange equilibrium constants), as well as to parameterize the adaptation to the external stimulus. We also visualized the physicochemical driving forces for the process by structural analysis using NMR spectroscopy and molecular modeling. This knowledge permitted the full understanding of the whole dynamic ...Continue Reading

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Citations

May 4, 2016·Chemical Reviews·Frank Biedermann, Hans-Jörg Schneider
Apr 1, 2017·Chemical Communications : Chem Comm·Joan AtcherIgnacio Alfonso
Nov 13, 2015·Chemical Communications : Chem Comm·Ignacio Alfonso
Jun 21, 2019·Chemical Communications : Chem Comm·Anna Serra-PontCiril Jimeno
Apr 4, 2020·Angewandte Chemie·Marion KiefferJonathan R Nitschke
Sep 5, 2015·Angewandte Chemie·Rakesh MukherjeeGonen Ashkenasy
May 10, 2017·Chemistry : a European Journal·Angel M ValdivielsoIgnacio Alfonso
May 24, 2020·Chemistry : a European Journal·Dennis Larsen, Sophie R Beeren
Jun 12, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Keiko YoneyamaAkiharu Satake
Dec 6, 2017·Chemistry : a European Journal·Carlo BravinCristiano Zonta
Sep 26, 2020·Chemical Communications : Chem Comm·Jordi SolàIgnacio Alfonso
Jun 15, 2021·Chemical Science·Carlo Bravin, Christopher A Hunter

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