Published in

American Association for the Advancement of Science, Science, 6446(364), p. 1166-1169, 2019

DOI: 10.1126/science.aaw1143

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Photoexcitation of flavoenzymes enables a stereoselective radical cyclization

This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

Light teaches (co)enzymes new tricks Light is widely used in organic synthesis to excite electrons in a substrate or catalyst, opening up reactive pathways to a desired product. Biology uses light sparingly in this way, but coenzymes such as flavin can be driven to excited states by light. Biegasiewicz et al. investigated this reactivity and found a suite of flavoenzymes that catalyze asymmetric radical cyclization when exposed to light. “Ene”-reductases, when reduced and illuminated, converted starting materials containing an α-chloroamide and an alkene into five-, six-, seven-, or eight-membered lactams. Different enzymes furnished different stereochemistry in the products, likely because of changes in active-site pocket geometry. Science , this issue p. 1166