Biocatalytic Enantioselective Oxidative CC Coupling by Aerobic CH Activation

Bridging the gap: The berberine bridge enzyme (BBE) was employed for the first preparative oxidative biocatalytic CC coupling that leads to a new intramolecular bond. This unique transformation requires O2 as sole stoichiometric oxidant and gives access to novel optically pure (S)‐berbine 2 and (R)...

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Published inAngewandte Chemie (International ed.) Vol. 50; no. 5; pp. 1068 - 1071
Main Authors Schrittwieser, Joerg H, Resch, Verena, Sattler, Johann H, Lienhart, Wolf-Dieter, Durchschein, Katharina, Winkler, Andreas, Gruber, Karl, Macheroux, Peter, Kroutil, Wolfgang
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.02.2011
WILEY-VCH Verlag
WILEY‐VCH Verlag
Wiley
Subjects
alkaloids
asymmetric synthesis
Benzylisoquinolines - chemical synthesis
Benzylisoquinolines - chemistry
Berberine Alkaloids - chemical synthesis
Berberine Alkaloids - chemistry
Biocatalysis
Chemistry
Chemistry, Multidisciplinary
Combinatorial Chemistry Techniques
CC coupling
CH activation
enzyme catalysis
Oxidative Coupling
Oxidoreductases, N-Demethylating - chemistry
Oxygen - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
C-C coupling
ASYMMETRIC-SYNTHESIS
HYDROGENATION
TETRAHYDROISOQUINOLINES
alkaloids
ISOQUINOLINE ALKALOIDS
DIHYDROISOQUINOLINES
enzyme catalysis
TERMINAL ALKYNES
BENZYLISOQUINOLINE ALKALOIDS
asymmetric synthesis
C-H activation
CHEMOENZYMATIC SYNTHESIS
BERBERINE BRIDGE ENZYME
GREEN CHEMISTRY
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Summary:Bridging the gap: The berberine bridge enzyme (BBE) was employed for the first preparative oxidative biocatalytic CC coupling that leads to a new intramolecular bond. This unique transformation requires O2 as sole stoichiometric oxidant and gives access to novel optically pure (S)‐berbine 2 and (R)‐1‐benzyl‐1,2,3,4‐tetrahydroisoquinoline 1 alkaloid derivatives by kinetic resolution.
Bibliography:http://dx.doi.org/10.1002/anie.201006268
ArticleID:ANIE201006268
istex:E048946749C8DDE48641DC106AD2D1622378A67E
European Commission - No. 238531
Austrian Science Fund - No. P20903-N17; No. P22115-N17
This study was financed by the Austrian Science Fund (FWF Project P20903-N17 and P22115-N17). We thank the European Commission (MC-ITN Biotrains, grant agreement no.: 238531) for financial support. We thank Christoph Göbl for measuring CD spectra and Bernd Werner for NMR measurements.
ark:/67375/WNG-B5178PQL-7
These authors contributed equally to this work.
This study was financed by the Austrian Science Fund (FWF Project P20903‐N17 and P22115‐N17). We thank the European Commission (MC‐ITN Biotrains, grant agreement no.: 238531) for financial support. We thank Christoph Göbl for measuring CD spectra and Bernd Werner for NMR measurements.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201006268