ArticleThe Journal of organic chemistry2011
Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids.
Article in The Journal of organic chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Novel Halolactones Derived from Vanillin: Design, Synthesis, Structural Characterization, and Evaluation of Antiproliferative and Hemolytic Activities.Molecules (Basel, Switzerland) · 2025Article
- Metabolomics and transcriptomics reveal the mechanism of alkaloid synthesis in Corydalis yanhusuo bulbs.PloS one · 2024Article
- Alkaloids inFrontiers in pharmacology · 2024Review
- Concise synthesis of (Chemical science · 2023Article
- Alkaloids ofBiomolecules · 2022Article
- Closing the gap: yeast electron-transferring flavoprotein links the oxidation of d-lactate and d-α-hydroxyglutarate to energy production via the respiratory chain.The FEBS journal · 2019Article
- The single berberine bridge enzyme homolog of Physcomitrella patens is a cellobiose oxidase.The FEBS journal · 2018Article
- Comparative study on alkaloids and their anti-proliferative activities from three Zanthoxylum species.BMC complementary and alternative medicine · 2017Article
- Improved simplicity and practicability in copper-catalyzed alkynylation of tetrahydroisoquinoline.Monatshefte fur chemie · 2017Article
- Structure and biochemical properties of recombinant human dimethylglycine dehydrogenase and comparison to the disease-related H109R variant.The FEBS journal · 2016Article
- Building Bridges: Biocatalytic C-C-Bond Formation toward Multifunctional Products.ACS catalysis · 2016Review
- Structure of a Berberine Bridge Enzyme-Like Enzyme with an Active Site Specific to the Plant Family Brassicaceae.PloS one · 2016Article
- Optimization of yeast-based production of medicinal protoberberine alkaloids.Microbial cell factories · 2015Article
- Oxidation of Monolignols by Members of the Berberine Bridge Enzyme Family Suggests a Role in Plant Cell Wall Metabolism.The Journal of biological chemistry · 2015Article
- Deracemization by simultaneous bio-oxidative kinetic resolution and stereoinversion.Angewandte Chemie (International ed. in English) · 2014Article
- The role of biocatalysis in the asymmetric synthesis of alkaloids.RSC advances · 2013Review
- Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1Tetrahedron, asymmetry · 2013Article
- Asymmetric Preparation ofOrganic process research & development · 2013Article
- Inverting the regioselectivity of the berberine bridge enzyme by employing customized fluorine-containing substrates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2012Article
- Catalytic and structural role of a conserved active site histidine in berberine bridge enzyme.Biochemistry · 2012Article
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8 authors.
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Abstract
A chemoenzymatic approach for the asymmetric total synthesis of the title compounds is described that employs an enantioselective oxidative C-C bond formation catalyzed by berberine bridge enzyme (BBE) in the asymmetric key step. This unique reaction yielded enantiomerically pure (R)-benzylisoquinoline derivatives and (S)-berbines such as the natural product (S)-scoulerine, a sedative and muscle relaxing agent. The racemic substrates rac-1 required for the biotransformation were prepared in 4-8 linear steps using either a Bischler-Napieralski cyclization or a C1-Cα alkylation approach. The chemoenzymatic synthesis was applied to the preparation of fourteen enantiomerically pure alkaloids, including the natural products (S)-scoulerine and (R)-reticuline, and gave overall yields of up to 20% over 5-9 linear steps.
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