Author: ["Yiyun Chen","Adam S. Kamlet","Jonathan B. Steinman","David R. Liu"]
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Abstract
Using a system that accelerates the serendipitous discovery of new reactions by evaluating hundreds of DNA-encoded substrate combinations in a single experiment, we explored a broad range of reaction conditions for new bond-forming reactions. We discovered reactivity that led to a biomolecule-compatible, Ru(II)-catalysed azide-reduction reaction induced by visible light. In contrast to current azide-reduction methods, this reaction is highly chemoselective and is compatible with alcohols, phenols, acids, alkenes, alkynes, aldehydes, alkyl halides, alkyl mesylates and disulfides. The remarkable functional group compatibility and mild conditions of the reaction enabled the azide reduction of nucleic acid and oligosaccharide substrates, with no detectable occurrence of side reactions. The reaction was also performed in the presence of a protein enzyme without the loss of enzymatic activity, in contrast to two commonly used azide-reduction methods. The visible-light dependence of this reaction provides a means of photouncaging functional groups, such as amines and carboxylates, on biological macromolecules without using ultraviolet irradiation. A DNA-encoded reaction discovery system has revealed reactivity that led to the development of a visible-light-induced, biomolecule-compatible azide reduction. This reaction exhibits remarkable chemoselectivity and can be performed on oligonucleotide and oligosaccharide substrates, and in the presence of a protein enzyme, without undesired side reactions or loss of enzyme activity.Cite this article
Chen, Y., Kamlet, A., Steinman, J. et al. A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system. Nature Chem 3, 146–153 (2011). https://doi.org/10.1038/nchem.932 