Simultaneous disulfide and boronic acid ester exchange in dynamic combinatorial libraries

TY - JOUR

T1 - Simultaneous disulfide and boronic acid ester exchange in dynamic combinatorial libraries

AU - Diemer, Sanna L.

AU - Kristensen, Morten

AU - Rasmussen, Brian

AU - Beeren, Sophie R.

AU - Pittelkow, Michael

N1 - Special issue: Supramolecular interactions

PY - 2015/9/10

Y1 - 2015/9/10

N2 - 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.

AB - 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.

U2 - 10.3390/ijms160921858

DO - 10.3390/ijms160921858

M3 - Journal article

C2 - 26378519

SN - 1661-6596

VL - 16

SP - 21858

EP - 21872

JO - International Journal of Molecular Sciences (Online)

JF - International Journal of Molecular Sciences (Online)

IS - 9

ER -