ArticleCommunications chemistry2020
Single step syntheses of (1S)-aryl-tetrahydroisoquinolines by norcoclaurine synthases.
Article in Communications chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Transaminase and Norcoclaurine Synthase One-Pot Cascades Towards (1S)-Tetrahydroisoquinolines.Chembiochem : a European journal of chemical biology · 2026Article
- Characterisation of the N-Methyltransferase SgPsmC: Application in the Kinetic Resolution of Pyrroloindolines.Angewandte Chemie (International ed. in English) · 2026Article
- Metabolome and transcriptome association study reveals biosynthesis of specialized benzylisoquinoline alkaloids inChinese herbal medicines · 2025Article
- Highly Acidic Electron-Rich Brønsted Acids Accelerate Asymmetric Pictet-Spengler Reactions by Virtue of Stabilizing Cation-π Interactions.Journal of the American Chemical Society · 2024Article
- Understanding the Enzyme (Journal of chemical information and modeling · 2024Article
- Engineering a norcoclaurine synthase for one-step synthesis of (S)-1-aryl-tetrahydroisoquinolines.Bioresources and bioprocessing · 2023Article
- One-Pot Chemoenzymatic Cascade for the Enantioselective C(1)-Allylation of Tetrahydroisoquinolines.Journal of the American Chemical Society · 2023Article
- Methyltransferases: Functions and Applications.Chembiochem : a European journal of chemical biology · 2022Review
- New Trends and Future Opportunities in the Enzymatic Formation of C-C, C-N, and C-O bonds.Chembiochem : a European journal of chemical biology · 2022Review
- Review
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Authors and funding
11 authors.
Funding
Abstract
The 1-aryl-tetrahydroisoquinoline (1-aryl-THIQ) moiety is found in many biologically active molecules. Single enantiomer chemical syntheses are challenging and although some biocatalytic routes have been reported, the substrate scope is limited to certain structural motifs. The enzyme norcoclaurine synthase (NCS), involved in plant alkaloid biosynthesis, has been shown to perform stereoselective Pictet-Spengler reactions between dopamine and several carbonyl substrates. Here, benzaldehydes are explored as substrates and found to be accepted by both wild-type and mutant constructs of NCS. In particular, the variant M97V gives a range of (1 S)-aryl-THIQs in high yields (48-99%) and e.e.s (79-95%). A co-crystallised structure of the M97V variant with an active site reaction intermediate analogue is also obtained with the ligand in a pre-cyclisation conformation, consistent with (1 S)-THIQs formation. Selected THIQs are then used with catechol O-methyltransferases with exceptional regioselectivity. This work demonstrates valuable biocatalytic approaches to a range of (1 S)-THIQs.
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Registered trials
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