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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Simultaneous Disulfide and Boronic Acid Ester Exchange in Dynamic Combinatorial Libraries.

Sanna L Diemer¹, Morten Kristensen², Brian Rasmussen³

¹Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark. sanna.lund_diemer@roche.com.

International Journal of Molecular Sciences

|September 18, 2015

Summary

This study demonstrates the simultaneous operation of disulfide exchange and boronic ester transesterification within dynamic combinatorial libraries. This advancement expands the complexity and applications of supramolecular chemistry receptor discovery.

Keywords:

boronic acid esters boronic acids disulfides dynamic combinatorial chemistry reversible chemical reactions supramolecular chemistry thiols

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Area of Science:

Supramolecular Chemistry
Organic Chemistry
Chemical Synthesis

Background:

Dynamic combinatorial chemistry (DCC) utilizes reversible reactions for the discovery of complex receptors.
Dynamic combinatorial libraries (DCLs) rely on building block exchange for thermodynamic control.
Simultaneous operation of multiple reversible reactions in DCLs can significantly increase system complexity and applications.

Purpose of the Study:

To investigate the simultaneous function of disulfide exchange and boronic ester transesterification in DCLs.
To establish suitable reaction conditions for dual reversible reactions within a single DCL.
To identify appropriate analytical techniques for studying such complex systems.

Main Methods:

Exploration of reaction conditions for simultaneous disulfide exchange and boronic ester transesterification.
Utilizing analytical techniques to monitor and characterize the DCL system.
Investigating the thermodynamic control in a DCL with two independent reversible reactions.

Main Results:

Demonstrated successful simultaneous operation of disulfide exchange and boronic ester transesterification under specific conditions.
Established protocols for creating and analyzing DCLs with dual reversible reactions.
Showcased the increased complexity achievable in DCLs through the combination of these reactions.

Conclusions:

The simultaneous use of disulfide exchange and boronic ester transesterification is feasible in DCLs.
This approach enhances the potential for discovering intricate supramolecular receptors.
Further research into multi-reaction DCLs promises expanded applications in chemistry.