Erdmann, Vanessa, Lichman, Benjamin R. orcid.org/0000-0002-0033-1120, Zhao, Jianxiong et al. (5 more authors) (2017) Enzymatic and Chemoenzymatic Three-Step Cascades for the Synthesis of Stereochemically Complementary Trisubstituted Tetrahydroisoquinolines. Angewandte Chemie - International Edition. pp. 12503-12507. ISSN 1433-7851
Abstract
Chemoenzymatic and enzymatic cascade reactions enable the synthesis of complex stereocomplementary 1,3,4-trisubstituted tetrahydroisoquinolines (THIQs) with three chiral centers in a step-efficient and selective manner without intermediate purification. The cascade employs inexpensive substrates (3-hydroxybenzaldehyde and pyruvate), and involves a carboligation step, a subsequent transamination, and finally a Pictet–Spengler reaction with a carbonyl cosubstrate. Appropriate selection of the carboligase and transaminase enzymes enabled the biocatalytic formation of (1R,2S)-metaraminol. Subsequent cyclization catalyzed either enzymatically by a norcoclaurine synthase or chemically by phosphate resulted in opposite stereoselectivities in the products at the C1 position, thus providing access to both orientations of the THIQ C1 substituent. This highlights the importance of selecting from both chemo- and biocatalysts for optimal results.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. |
Keywords: | asymmetric catalysis,biocatalysis,chemoenzymatic cascades,norcoclaurine synthase,transaminases |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Biology (York) |
Depositing User: | Pure (York) |
Date Deposited: | 06 Dec 2018 08:50 |
Last Modified: | 23 Jan 2025 00:17 |
Published Version: | https://doi.org/10.1002/anie.201705855 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1002/anie.201705855 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:139641 |
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