Biocatalytic C3-Indole Methylation—A Useful Tool for the Natural-Product-Inspired Stereoselective Synthesis of Pyrroloindoles,Angewandte Chemie International Edition

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Biocatalytic C3-Indole Methylation—A Useful Tool for the Natural-Product-Inspired Stereoselective Synthesis of Pyrroloindoles
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2021-08-16 , DOI: 10.1002/anie.202107619
Pascal Schneider ₁ , Birgit Henßen ₂ , Beatrix Paschold ₁ , Benjamin P Chapple ₁ , Marcel Schatton ₁ , Florian P Seebeck ₃ , Thomas Classen ₂ , Jörg Pietruszka _{1,

2}

Affiliation

Enantioselective synthesis of bioactive compounds bearing a pyrroloindole framework is often laborious. In contrast, there are several S-adenosyl methionine (SAM)-dependent methyl transferases known for stereo- and regioselective methylation at the C3 position of various indoles, directly leading to the formation of the desired pyrroloindole moiety. Herein, the SAM-dependent methyl transferase PsmD from Streptomyces griseofuscus, a key enzyme in the biosynthesis of physostigmine, is characterized in detail. The biochemical properties of PsmD and its substrate scope were demonstrated. Preparative scale enzymatic methylation including SAM regeneration was achieved for three selected substrates after a design-of-experiment optimization.

中文翻译：

生物催化 C3-吲哚甲基化——天然产物启发立体选择性合成吡咯并吲哚的有用工具

具有吡咯并吲哚骨架的生物活性化合物的对映选择性合成通常很费力。相比之下，有几种 S-腺苷甲硫氨酸 (SAM) 依赖性甲基转移酶已知可在各种吲哚的 C3 位上进行立体和区域选择性甲基化，直接导致所需吡咯并吲哚部分的形成。本文对来自灰褐链霉菌 (Streptomyces griseofuscus) 的 SAM 依赖性甲基转移酶 PsmD（毒扁豆碱生物合成中的关键酶）进行了详细表征。论证了 PsmD 的生化特性及其底物范围。经过实验设计优化后，三种选定底物实现了制备规模的酶促甲基化，包括 SAM 再生。

更新日期：2021-10-12

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