Simultaneous Disulfide and Boronic Acid Ester Exchange in Dynamic Combinatorial Libraries

Sanna L. Diemer, Morten Kristensen, Brian Rasmussen, Sophie R. Beeren, Michael Pittelkow

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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.
Original languageEnglish
JournalInternational Journal of Molecular Sciences
Volume16
Issue number9
Pages (from-to)21858-21872
Number of pages15
ISSN1661-6596
DOIs
Publication statusPublished - 2015

Keywords

  • Boronic acid esters
  • Boronic acids
  • Disulfides
  • Dynamic combinatorial chemistry
  • reversible chemical reactions
  • Supramolecular chemistry
  • Thiols

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