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Template effects of vesicles in dynamic covalent chemistry.

Accepted version
Peer-reviewed

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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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Keywords

3403 Macromolecular and Materials Chemistry, 34 Chemical Sciences

Journal Title

Chem Sci

Conference Name

Journal ISSN

2041-6520
2041-6539

Volume Title

11

Publisher

Royal Society of Chemistry (RSC)

Rights

All rights reserved
Sponsorship
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (837706)
Marie Skłodowska Curie Actions for Individual Fellowship (H2020-MSCA-IF-2018 number 837706).