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Expanding Reactivity in DNA-Encoded Library Synthesis via Reversible Binding of DNA to an Inert Quaternary Ammonium Support

preprint
submitted on 08.04.2019 and posted on 09.04.2019 by Dillon T. Flood, Shota Asai, Xuejing Zhang, Jie Wang, Leonard Yoon, Zoë C. Adams, Blythe C. Dillingham, Brittany Sanchez, Julien C. Vantourout, Mark E. Flanagan, David W. Piotrowski, Paul Richardson, Samantha Green, Ryan Shenvi, Jason Chen, Phil Baran, Philip Dawson
Herein, we present the adaptation of reversible adsorption to solid support (RASS) for a DEL setting, which allows reactions to be performed in organic solvents at near anhydrous conditions opening previously inaccessible chemical reactivities to DEL. The RASS approach enabled the rapid development of C(sp2)-C(sp3) decarboxylative cross-couplings with broad substrate scope, an electrochemical amination (the first electrochemical synthetic transformation performed in a DEL context), and improved reductive amination conditions. We believe that RASS will offer expedient access to new DEL reactivities, expanded chemical space, and ultimately more drug-like libraries.

Funding

NIH GM-118176

Pfizer

History

Email Address of Submitting Author

dawson@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0002-2538-603X

Declaration of Conflict of Interest

No conflict

Exports