A New Strategy for Aromatic Ring Alkylation in Cylindrocyclophane Biosynthesis

Overview

Journal Nat Chem Biol

Specialties Biochemistry
Biology
Chemistry

Date 2017 Jul 4

PMID 28671684

Citations 34

Authors

Hitomi Nakamura

Erica E Schultz

Emily P Balskus

Affiliations

Soon will be listed here.

Abstract

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.

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