Organic Chemistry

A light approach to diverse amino acids

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Science  19 Aug 2016:
Vol. 353, Issue 6301, pp. 787-788
DOI: 10.1126/science.353.6301.787-f

As the building blocks of all proteins, amino acids have long been a target of modification for chemists. Installing unnatural side chains can facilitate medicinal research, as well as fundamental studies of protein function and dynamics. Jiang et al. present a versatile method for replacing the natural side chains of aspartic and glutamic acid with a variety of ketones, esters, amides, and alkynes while preserving the original stereochemistry. A ruthenium catalyst excited by visible light spurs ejection of a phthalimide-activated acid group from the original side chain, leaving a reactive radical to bind the new substituent.

Sci. Rep. 10.1038/srep26161 (2016).

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