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.
Highlights
Dynamic combinatorial chemistry is a supramolecular methodology that enables the discovery of specific and high affinity receptors [1]
In a dynamic combinatorial libraries (DCLs) that makes use of two different reversible reactions, the reactions may be: (1) addressed simultaneously, where the reactions are reversible under the same reaction conditions; or (2) addressed orthogonally, where the two reactions are only reversible under different conditions
We have chosen to use phenylboronic acids, catechols (1,2-dihydroxy benzenes) and aromatic thiols to develop the conditions for the simultaneous exchange of disulfide and boronic ester building blocks in dynamic combinatorial chemistry (Figure 2)
Summary
Dynamic combinatorial chemistry is a supramolecular methodology that enables the discovery of specific and high affinity receptors [1]. With the aim of expanding the diversity in dynamic combinatorial libraries, we here introduce new double-level communicating DCLs in which reversible disulfide exchange and boronic ester transesterfication operate simultaneously (Figure 1). This type of DCL creates diversity in the library composition and opens up for the possibility of selecting supramolecular receptors the recognize guests using the integral features of the building blocks themselves, but the functional groups that make up the connectivity [13]. (a) disulfide formation and exchange; (b) boronic acid ester formation; and (c) simultaneous disulfide and boronic acid ester formation and exchange
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