ArticleBiochemistry2017
Structural Evidence for the Dopamine-First Mechanism of Norcoclaurine Synthase.
Article in Biochemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 52 citations in OpenAlex.
- Recent Progress in Catalytic Asymmetric Pictet-Spengler Reaction to Construct 1,1-Disubstituted Scaffolds.Synthesis · 2026Article
- Identification of a missing Pictet-Spenglerase in the Gloriosa superba L. colchicine biosynthesis pathway.Molecular biology reports · 2025Article
- Understanding the Enzyme (Journal of chemical information and modeling · 2024Article
- Computational mechanistic investigation of the kinetic resolution of α-methyl-phenylacetaldehyde by norcoclaurine synthase.Communications chemistry · 2024Article
- Rational Engineering of (Molecules (Basel, Switzerland) · 2023Article
- The Quantum Chemical Cluster Approach in Biocatalysis.Accounts of chemical research · 2023Review
- Engineering a norcoclaurine synthase for one-step synthesis of (S)-1-aryl-tetrahydroisoquinolines.Bioresources and bioprocessing · 2023Article
- Elucidation of the (R)-enantiospecific benzylisoquinoline alkaloid biosynthetic pathways in sacred lotus (Nelumbo nucifera).Scientific reports · 2023Article
- Elucidation of the 1-phenethylisoquinoline pathway from an endemic coniferProceedings of the National Academy of Sciences of the United States of America · 2023Article
- Characterization of norbelladine synthase and noroxomaritidine/norcraugsodine reductase reveals a novel catalytic route for the biosynthesis of Amaryllidaceae alkaloids including the Alzheimer's drug galanthamine.Frontiers in plant science · 2023Article
- Review
- Biosynthesis and synthetic biology of psychoactive natural products.Chemical Society reviews · 2021Review
- Single step syntheses of (1S)-aryl-tetrahydroisoquinolines by norcoclaurine synthases.Communications chemistry · 2020Article
- Over 100 Million Years of Enzyme Evolution Underpinning the Production of Morphine in the Papaveraceae Family of Flowering Plants.Plant communications · 2020Article
- Biomimetic Phosphate-Catalyzed Pictet-Spengler Reaction for the Synthesis of 1,1'-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids.The Journal of organic chemistry · 2019Article
- Benzylisoquinoline Alkaloids Biosynthesis in Sacred Lotus.Molecules (Basel, Switzerland) · 2018Review
- Asymmetric Synthesis of (R)-1-Alkyl-Substituted Tetrahydro-ß-carbolines Catalyzed by Strictosidine Synthases.Angewandte Chemie (International ed. in English) · 2018Article
- One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues.Chemical communications (Cambridge, England) · 2018Article
- Green Routes for the Production of Enantiopure Benzylisoquinoline Alkaloids.International journal of molecular sciences · 2017Review
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 1 country.
Funding
Abstract
Norcoclaurine synthase (NCS) is a Pictet-Spenglerase that catalyzes the first key step in plant benzylisoquinoline alkaloid metabolism, a compound family that includes bioactive natural products such as morphine. The enzyme has also shown great potential as a biocatalyst for the formation of chiral isoquinolines. Here we present new high-resolution X-ray crystallography data describing Thalictrum flavum NCS bound to a mechanism-inspired ligand. The structure supports two key features of the NCS "dopamine-first" mechanism: the binding of dopamine catechol to Lys-122 and the position of the carbonyl substrate binding site at the active site entrance. The catalytically vital residue Glu-110 occupies a previously unobserved ligand-bound conformation that may be catalytically significant. The potential roles of inhibitory binding and alternative amino acid conformations in the mechanism have also been revealed. This work significantly advances our understanding of the NCS mechanism and will aid future efforts to engineer the substrate scope and catalytic properties of this useful biocatalyst.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.