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 |
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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