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Photoexcitation of flavoenzymes enables a stereoselective radical cyclization

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Science  21 Jun 2019:
Vol. 364, Issue 6446, pp. 1166-1169
DOI: 10.1126/science.aaw1143

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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

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