Template effects of vesicles in dynamic covalent chemistry.

Chemical Science
Carlo Bravin, Christopher A Hunter

Abstract

Vesicle lipid bilayers have been employed as templates to modulate the product distribution in a dynamic covalent library of Michael adducts formed by mixing a Michael acceptor with thiols. In methanol solution, all possible Michael adducts were obtained in similar amounts. Addition of vesicles to the dynamic covalent library led to the formation of a single major product. The equilibrium constants for formation of the Michael adducts are similar for all of the thiols used in this experiment, and the effect of the vesicles on the composition of the library is attributed to the differential partitioning of the library members between the lipid bilayer and the aqueous solution. The results provide a quantitative approach for exploiting dynamic covalent chemistry within lipid bilayers.

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Citations

Jun 25, 2021·Chemical Science·Yangyang ChengStefan Matile
Apr 25, 2021·Journal of Colloid and Interface Science·Yiqian XieJian Xu
Jun 5, 2021·Angewandte Chemie·Tanausú SantosRomen Carrillo
Sep 2, 2021·JACS Au·Quentin LaurentStefan Matile

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