Nature Chemical Biology
Nature Chemical Biology
5 years ago

A new strategy for aromatic ring alkylation in cylindrocyclophane biosynthesis

A new strategy for aromatic ring alkylation in cylindrocyclophane biosynthesis
Hitomi Nakamura, Erica E Schultz, Emily P Balskus
Alkylation of aromatic rings with alkyl halides is an important transformation in organic synthesis, yet an enzymatic equivalent is unknown. Here, we report that cylindrocyclophane biosynthesis in Cylindrospermum licheniforme ATCC 29412 involves chlorination of an unactivated carbon center by a novel halogenase, followed by a previously uncharacterized enzymatic dimerization reaction featuring sequential, stereospecific alkylations of resorcinol aromatic rings. Discovery of the enzymatic machinery underlying this unique biosynthetic carbon–carbon bond formation has implications for biocatalysis and metabolic engineering.

Publisher URL: http://dx.doi.org/10.1038/nchembio.2421

DOI: 10.1038/nchembio.2421

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