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Biocatalytic production of tetrahydroisoquinolines
Authors:Ruff Bettina M  Bräse S  O'Connor Sarah E
Affiliation:a Massachusetts Institute of Technology, Department of Chemistry, 77 Massachusetts Avenue, Cambridge, MA 02139, USA
b Karlsruhe Institute of Technology, Institute of Organic Chemistry, Fritz-Haber-Weg 6, 76137 Karlsruhe, Germany
c The John Innes Centre, Department of Biological Chemistry, Norwich NR4 7UH, UK
d The University of East Anglia, Norwich NR4 7TJ, UK
Abstract:The promiscuity of the enzyme norcoclaurine synthase is described. This biocatalyst yielded a diverse array of substituted tetrahydroisoquinolines by cyclizing dopamine with various acetaldehydes in a Pictet-Spengler reaction. This enzymatic reaction may provide a biocatalytic route to a range of tetrahydroisoquinoline alkaloids.
Keywords:Biocatalysis   Pictet-Spengler reaction   Norcoclaurine synthase   Tetrahydroisoquinoline alkaloids
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