A new strategy for aromatic ring alkylation in cylindrocyclophane biosynthesis

被引：65

作者：

Nakamura, Hitomi ^{[1
]}

Schultz, Erica E. ^{[1
]}

Balskus, Emily P. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

NATURE CHEMICAL BIOLOGY | 2017年 / 13卷 / 08期

基金：

美国国家科学基金会;

关键词：

FRIEDEL-CRAFTS ALKYLATION; N-OXYGENASE AURF; CRYSTAL-STRUCTURE; CYANOBACTERIUM; ENZYME; DOMAIN; ACID; MEROCYCLOPHANES; HALOGENATION; PEPTIDES;

D O I：

10.1038/nchembio.2421

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

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.

引用

页码：916 / +

页数：11

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