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Biocatalytic Routes to Enantiomerically Enriched Dibenz[c,e]azepines

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Author(s)

  • Scott P. France
  • Godwin A Aleku
  • Mahima Sharma
  • Juan Mangas-Sanchez
  • Roger M Howard
  • Jeremy Steflik
  • Rajesh Kumar
  • Ralph W Adams
  • Iustina Slabu
  • Robert Crook
  • Gideon Grogan
  • Timothy W Wallace
  • Nicholas John Turner

Department/unit(s)

Publication details

JournalAngewandte Chemie International Edition
DateAccepted/In press - 10 Oct 2017
DateE-pub ahead of print - 7 Nov 2017
DatePublished (current) - 4 Dec 2017
Issue number49
Volume56
Number of pages5
Pages (from-to)15589-15593
Early online date7/11/17
Original languageEnglish

Abstract

Biocatalytic retrosynthetic analysis of dibenz[c,e]azepines has highlighted the use of imine reductase (IRED) and ω-transaminase (ω-TA) biocatalysts to establish the key stereocentres of these molecules. Several enantiocomplementary IREDs were identified for the synthesis of (R)- and (S)-5-methyl-6,7-dihydro-5H-dibenz[c,e]azepine with excellent enantioselectivity, by reduction of the parent imines. Crystallographic evidence suggests that IREDs may be able to bind one conformer of the imine substrate such that, upon reduction, the major product conformer is generated directly. ω-TA biocatalysts were also successfully employed for the production of enantiopure 1-(2-bromophenyl)ethan-1-amine, thus enabling an orthogonal route for the installation of chirality into dibenz[c,e]azepine framework.

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© 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

    Research areas

  • biocatalysis, heterocycles, reductases, synthetic methods, transaminases

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