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使用特定生物催化剂不对称制备α-、β-和γ-胺。

Asymmetric Preparation of -, -, and -Amines Employing Selected Biocatalysts.

作者信息

Kroutil Wolfgang, Fischereder Eva-Maria, Fuchs Christine S, Lechner Horst, Mutti Francesco G, Pressnitz Desiree, Rajagopalan Aashrita, Sattler Johann H, Simon Robert C, Siirola Elina

机构信息

Department of Chemistry, University of Graz , Heinrichstrasse 28, A-8010 Graz, Austria ; ACIB GmbH c/o Department of Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria.

出版信息

Org Process Res Dev. 2013 May 17;17(5):751-759. doi: 10.1021/op4000237. Epub 2013 Apr 22.

DOI:10.1021/op4000237
PMID:23794796
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3688330/
Abstract

This account focuses on the application of ω-transaminases, lyases, and oxidases for the preparation of amines considering mainly work from our own lab. Examples are given to access α-chiral primary amines from the corresponding ketones as well as terminal amines from primary alcohols via a two-step biocascade. 2,6-Disubstituted piperidines, as examples for secondary amines, are prepared by biocatalytical regioselective asymmetric monoamination of designated diketones followed by spontaneous ring closure and a subsequent diastereoselective reduction step. Optically pure -amines such as berbines and -methyl benzylisoquinolines are obtained by kinetic resolution via an enantioselective aerobic oxidative C-C bond formation.

摘要

本综述主要基于我们实验室的研究工作，重点关注ω-转氨酶、裂解酶和氧化酶在胺类制备中的应用。文中给出了通过两步生物级联反应从相应酮制备α-手性伯胺以及从伯醇制备末端胺的实例。作为仲胺的示例，2,6-二取代哌啶是通过对特定二酮进行生物催化区域选择性不对称单胺化，随后自发闭环并进行后续非对映选择性还原步骤制备的。光学纯的 -胺类，如小檗碱和 -甲基苄基异喹啉，是通过对映选择性需氧氧化C-C键形成的动力学拆分获得的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b3a/3688330/675523711db8/op-2013-000237_0013.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b3a/3688330/3e9545d8ed97/op-2013-000237_0003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b3a/3688330/18a610b18b66/op-2013-000237_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b3a/3688330/e84555e2c7b8/op-2013-000237_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b3a/3688330/3dc5b4d4f1d1/op-2013-000237_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b3a/3688330/46d7b22ad787/op-2013-000237_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b3a/3688330/6d4afac65aff/op-2013-000237_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b3a/3688330/82de335c6541/op-2013-000237_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b3a/3688330/d9cf024a8994/op-2013-000237_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b3a/3688330/aa5c318d85ab/op-2013-000237_0012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b3a/3688330/675523711db8/op-2013-000237_0013.jpg

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