A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system.
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.
Howard Hughes Medical Institute, Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA.
Yiyun
Y
Chen
Adam S
AS
Kamlet
Jonathan B
JB
Steinman
David R
DR
Liu
D001386:Azides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D008027:Light; D015394:Molecular Structure; D020411:Oligonucleotide Array Sequence Analysis; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry*
D001386:Azides; D002264:Carboxylic Acids; D012428:Ruthenium; D004247:DNA
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