Enzymatic Desymmetrising Redox Reactions for the Asymmetric Synthesis of Biaryl Atropisomers

Samantha Staniland, Bo Yuan, Nelson Giménez-Agullõ, Tommaso Marcelli, Simon C. Willies, Damian M. Grainger, Nicholas J. Turner*, Jonathan Clayden

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

16 Citations (Scopus)

Abstract

Atropisomeric biaryls carrying ortho-hydroxymethyl and formyl groups were made enantioselectively by desymmetrisation of dialdehyde or diol substrates. The oxidation of the symmetrical diol substrates was achieved using a variant of galactose oxidase (GOase), and the reduction of the dialdehydes using a panel of ketoreductases. Either M or P enantiomers of the products could be formed, with absolute configurations assigned by time-dependent DFT calculations of circular dichroism spectra. The differing selectivities observed with different biaryl structures offer an insight into the detailed structure of the active site of the GOase enzyme.

Original languageEnglish
Pages (from-to)13084-13088
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number41
Early online date22 Aug 2014
DOIs
Publication statusPublished - 6 Oct 2014

Keywords

  • atropisomerism
  • biaryls
  • biocatalysis
  • galactose oxidase
  • ketoreductase

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    Staniland, S., Yuan, B., Giménez-Agullõ, N., Marcelli, T., Willies, S. C., Grainger, D. M., Turner, N. J., & Clayden, J. (2014). Enzymatic Desymmetrising Redox Reactions for the Asymmetric Synthesis of Biaryl Atropisomers. Chemistry - A European Journal, 20(41), 13084-13088. https://doi.org/10.1002/chem.201404509