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One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine

Lichman, BR; Lamming, ED; Pesnot, T; Smith, JM; Hailes, HC; Ward, JM; (2014) One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine. Green Chemistry , 17 (2) pp. 852-855. 10.1039/c4gc02325k. Green open access

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Abstract

We describe novel chemoenzymatic routes to (S)-benzylisoquinoline and (S)-tetrahydroprotoberberine alkaloids using the enzymes transaminase (TAm) and norcoclaurine synthase (NCS) in a one-pot, one-substrate ‘triangular’ cascade. Employment of up to two C–C bond forming steps allows for the rapid generation of molecular complexity under mild conditions.

Type: Article
Title: One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c4gc02325k
Publisher version: https://doi.org/10.1039/c4gc02325k
Language: English
Additional information: This work is licensed under a Creative Commons Attribution 3.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/3.0/
Keywords: Science & Technology, Physical Sciences, Chemistry, Multidisciplinary, GREEN & SUSTAINABLE SCIENCE & TECHNOLOGY, Chemistry, Science & Technology - Other Topics, ENGINEERED ESCHERICHIA-COLI, PICTET-SPENGLER REACTION, BENZYLISOQUINOLINE ALKALOIDS, ORGANIC-SYNTHESIS, SACCHAROMYCES-CEREVISIAE, ASYMMETRIC-SYNTHESIS, TETRAHYDROISOQUINOLINES, TETRAHYDROPAPAVEROLINE, MORPHINE, BIOTRANSFORMATION
UCL classification: UCL
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science > Dept of Biochemical Engineering
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10065063
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