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 language | English |
|---|---|
| Pages (from-to) | 13084-13088 |
| Number of pages | 5 |
| Journal | Chemistry - A European Journal |
| Volume | 20 |
| Issue number | 41 |
| Early online date | 22 Aug 2014 |
| DOIs | |
| Publication status | Published - 6 Oct 2014 |
Keywords
- atropisomerism
- biaryls
- biocatalysis
- galactose oxidase
- ketoreductase
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Cite this
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