ACIB GmbH, Petersgasse 14, 8010, Graz, Austria.
Institute of Chemistry, University of Graz, NAWI Graz, BioTechMed Graz, Heinrichstraße 28, 8010, Graz, Austria.
Angew Chem Int Ed Engl. 2017 Jun 19;56(26):7615-7619. doi: 10.1002/anie.201703270. Epub 2017 May 23.
The Friedel-Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel-Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries rearrangement-like reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C-C bond formation methods.
弗里德尔-克拉夫茨酰化反应通常用于芳基酮的合成，而尚未引入可能受益于酶的化学和区域选择性的生物催化版本。本文描述了一种细菌酰基转移酶，它可以在缓冲液中催化酚类底物的弗里德尔-克拉夫茨 C-酰化，而不需要辅酶 A 激活的试剂。转化率高达>99%，并且该酶接受各种 C 或 O-酰基供体，如 DAPG 或异丙烯基乙酸酯。此外，该酶还能使间苯二酚衍生物发生类似于 Frie 重排的反应。这些发现为开发替代的和选择性的 C-C 键形成方法开辟了道路。
