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Int. J. Mol. Sci. 2015, 16(9), 21858-21872; doi:10.3390/ijms160921858

Simultaneous Disulfide and Boronic Acid Ester Exchange in Dynamic Combinatorial Libraries

1
Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark
2
Department of Chemistry, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark
*
Authors to whom correspondence should be addressed.
Academic Editors: John George Hardy and Max von Delius
Received: 20 July 2015 / Revised: 18 August 2015 / Accepted: 1 September 2015 / Published: 10 September 2015
(This article belongs to the Special Issue Supramolecular Interactions)
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Abstract

Dynamic combinatorial chemistry has emerged as a promising tool for the discovery of complex receptors in supramolecular chemistry. At the heart of dynamic combinatorial chemistry are the reversible reactions that enable the exchange of building blocks between library members in dynamic combinatorial libraries (DCLs) ensuring thermodynamic control over the system. If more than one reversible reaction operates in a single dynamic combinatorial library, the complexity of the system increases dramatically, and so does its possible applications. One can imagine two reversible reactions that operate simultaneously or two reversible reactions that operate independently. Both these scenarios have advantages and disadvantages. In this contribution, we show how disulfide exchange and boronic ester transesterification can function simultaneous in dynamic combinatorial libraries under appropriate conditions. We describe the detailed studies necessary to establish suitable reaction conditions and highlight the analytical techniques appropriate to study this type of system. View Full-Text
Keywords: dynamic combinatorial chemistry; supramolecular chemistry; disulfides; thiols; boronic acids; boronic acid esters; reversible chemical reactions dynamic combinatorial chemistry; supramolecular chemistry; disulfides; thiols; boronic acids; boronic acid esters; reversible chemical reactions
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MDPI and ACS Style

Diemer, S.L.; Kristensen, M.; Rasmussen, B.; Beeren, S.R.; Pittelkow, M. Simultaneous Disulfide and Boronic Acid Ester Exchange in Dynamic Combinatorial Libraries. Int. J. Mol. Sci. 2015, 16, 21858-21872.

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