Enzymatic oxidation of para-substituted arenes: access to new non-racemic chiral metabolites for synthesis |
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Authors: | John F Trant Jordan Froese Tomas Hudlicky |
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Institution: | Department of Chemistry and Centre for Biotechnology, Brock University, 500 Glenridge Avenue, St Catharines, Ontario, Canada L2S 3A1 |
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Abstract: | A series of para-substituted benzene derivatives were subjected to whole-cell fermentation with Escherichia coli JM109 (pDTG601), an organism expressing toluene dioxygenase (TDO). Several compounds proved to be excellent substrates for TDO, including 4-bromo-phenylacetylene, 4-bromobenzaldehyde, 4-bromobenzyl alcohol and 4-bromo-allylbenzene. Some of the first para-functionalized diene diols produced using TDO, are useful substrates for further synthetic manipulations, including their use in the potential synthesis of complex natural products. |
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