Expanding Reactivity in DNA-Encoded Library Synthesis via Reversible Binding of DNA to an Inert Quaternary Ammonium Support Article Swipe
Dillon T. Flood
,
Shota Asai
,
Xue‐Jing Zhang
,
Jie Wang
,
Leonard Yoon
,
Zoë C. Adams
,
Blythe C. Dillingham
,
Brittany B. Sanchez
,
Julien C. Vantourout
,
Mark E. Flanagan
,
David W. Piotrowski
,
Paul Richardson
,
Samantha A. Green
,
Ryan A. Shenvi
,
Jason S. Chen
,
Phil S. Baran
,
Philip E. Dawson
·
YOU?
·
· 2019
· Open Access
·
· DOI: https://doi.org/10.1021/jacs.9b03774
YOU?
·
· 2019
· Open Access
·
· DOI: https://doi.org/10.1021/jacs.9b03774
DNA Encoded Libraries have proven immensely powerful tools for lead identification. The ability to screen billions of compounds at once has spurred increasing interest in DEL development and utilization. Although DEL provides access to libraries of unprecedented size and diversity, the idiosyncratic and hydrophilic nature of the DNA tag severely limits the scope of applicable chemistries. It is known that biomacromolecules can be reversibly, noncovalently adsorbed and eluted from solid supports, and this phenomenon has been utilized to perform synthetic modification of biomolecules in a strategy we have described as reversible adsorption to solid support (RASS). Herein, we present the adaptation of 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. The utility of these reactions was demonstrated through a DEL-rehearsal in which all newly developed chemistries were orchestrated to afford a compound rich in diverse skeletal linkages. We believe that RASS will offer expedient access to new DEL reactivities, expanded chemical space, and ultimately more drug-like libraries.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/jacs.9b03774
- OA Status
- green
- Cited By
- 146
- References
- 47
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W2947079937
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W2947079937Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1021/jacs.9b03774Digital Object Identifier
- Title
-
Expanding Reactivity in DNA-Encoded Library Synthesis via Reversible Binding of DNA to an Inert Quaternary Ammonium SupportWork title
- Type
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articleOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2019Year of publication
- Publication date
-
2019-05-28Full publication date if available
- Authors
-
Dillon T. Flood, Shota Asai, Xue‐Jing Zhang, Jie Wang, Leonard Yoon, Zoë C. Adams, Blythe C. Dillingham, Brittany B. Sanchez, Julien C. Vantourout, Mark E. Flanagan, David W. Piotrowski, Paul Richardson, Samantha A. Green, Ryan A. Shenvi, Jason S. Chen, Phil S. Baran, Philip E. DawsonList of authors in order
- Landing page
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https://doi.org/10.1021/jacs.9b03774Publisher landing page
- Open access
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YesWhether a free full text is available
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greenOpen access status per OpenAlex
- OA URL
-
https://figshare.com/articles/journal_contribution/Expanding_Reactivity_in_DNA-Encoded_Library_Synthesis_via_Reversible_Binding_of_DNA_to_an_Inert_Quaternary_Ammonium_Support/8263736Direct OA link when available
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Chemistry, Biomolecule, Anhydrous, Combinatorial chemistry, DNA, Reactivity (psychology), Nanotechnology, Organic chemistry, Biochemistry, Pathology, Medicine, Materials science, Alternative medicineTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
146Total citation count in OpenAlex
- Citations by year (recent)
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2025: 11, 2024: 22, 2023: 18, 2022: 20, 2021: 32Per-year citation counts (last 5 years)
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47Number of works referenced by this work
- Related works (count)
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10Other works algorithmically related by OpenAlex
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