A new strategy for aromatic ring alkylation in cylindrocyclophane biosynthesis

作者:Nakamura Hitomi; Schultz Erica E; Balskus Emily P
来源:Nature Chemical Biology, 2017, 13(8): 916-+.
DOI:10.1038/nchembio.2421

摘要

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.

  • 出版日期2017-8