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DNA-Compatible Nitro Reduction and Synthesis of Benzimidazoles.

Authors
  • Du, Huang-Chi1
  • Huang, Hongbing1
  • 1 Center for Drug Discovery, Department of Pathology and Immunology, Baylor College of Medicine , Houston, Texas 77030, United States. , (United States)
Type
Published Article
Journal
Bioconjugate Chemistry
Publisher
American Chemical Society
Publication Date
Oct 18, 2017
Volume
28
Issue
10
Pages
2575–2580
Identifiers
DOI: 10.1021/acs.bioconjchem.7b00416
PMID: 28841007
Source
Medline
License
Unknown

Abstract

DNA-encoded chemical libraries have emerged as a cost-effective alternative to high-throughput screening (HTS) for hit identification in drug discovery. A key factor for productive DNA-encoded libraries is the chemical diversity of the small molecule moiety attached to an encoding DNA oligomer. The library structure diversity is often limited to DNA-compatible chemical reactions in aqueous media. Herein, we describe a facile process for reducing aryl nitro groups to aryl amines. The new protocol offers simple operation and circumvents the pyrophoric potential of the conventional method (Raney nickel). The reaction is performed in aqueous solution and does not compromise DNA structural integrity. The utility of this method is demonstrated by the versatile synthesis of benzimidazoles on DNA.

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