DNA-Compatible Nitro Reduction and Synthesis of Benzimidazoles

Huang-Chi Du; Ying-Chu Chen; Hongbing Huang

doi:10.1007/978-1-0716-2545-3_11

DNA-Compatible Nitro Reduction and Synthesis of Benzimidazoles

Methods Mol Biol. 2022:2541:67-73. doi: 10.1007/978-1-0716-2545-3_11.

Authors

Huang-Chi Du¹, Ying-Chu Chen¹, Hongbing Huang²

Affiliations

¹ Center for Drug Discovery, Department of Pathology and Immunology, Baylor College of Medicine, Houston, TX, USA.
² Center for Drug Discovery, Department of Pathology and Immunology, Baylor College of Medicine, Houston, TX, USA. Hongbing.huang@gmail.com.

PMID: 36083546
DOI: 10.1007/978-1-0716-2545-3_11

Abstract

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 by using sodium dithionite (Na₂S₂O₄). The new protocol offers simple operation and circumvents the pyrophoric potential of the conventional method (Raney nickel). The utility of this method is demonstrated by the versatile synthesis of benzimidazoles on DNA.

Keywords: Benzimidazoles; DNA-compatible reaction; Nitro reduction; Sodium dithionite.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines / chemistry
Benzimidazoles* / chemistry
DNA / chemistry
DNA / genetics
Gene Library
Small Molecule Libraries* / chemistry

Substances

Amines
Benzimidazoles
Small Molecule Libraries
DNA