| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345779 | Tetrahedron: Asymmetry | 2013 | 7 Pages |
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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(1R,2R)-3-Bromo-6-ethynylcyclohexa-3,5-diene-1,2-diolC8H7BrO2er 95:5[α]D20=+34.6 (c 0.5, MeOH)Source of chirality: Enzymatic dihydroxylation by TDO (1-bromo-4-ethynylbenzene)Absolute configuration: (1R,2R)
(1R,2R)-3-Allyl-6-bromocyclohexa-3,5-diene-1,2-diolC9H11BrO2er 81.5:18.5[α]D20=+13.6 (c 0.86, MeOH)Source of chirality: Enzymatic dihydroxylation by TDO (1-bromo-4-allylbenzene)Absolute configuration: (1R,2R)
(1R,2R)-3-Bromo-6-(hydroxymethyl)cyclohexa-3,5-diene-1,2-diolC7H9BrO3er 78:22[α]D20=-8.3 (c 1.0, MeOH)Source of chirality: Enzymatic dihydroxylation by TDO (4-bromobenzyl alcohol)Absolute configuration: (1R,2R)
(1S,2R,3R)-3-Ethyl-[1,2]-isopropylidenedioxycyclohexaneC11H20O2er >99:1[α]D20=+10.9 (c 1.0, CHCl3)Source of chirality: Enzymatic dihydroxylation by TDO (ethylbenzene)Absolute configuration: (1R,2R)
(1S,2R,3S)-3-Hydroxymethyl-[1,2]-isopropylidenedioxycyclohexaneC9H15O3er 78:22[α]D20=-6.1 (c 2.0, CHCl3)Source of chirality: Enzymatic dihydroxylation by TDO (4-bromobenzyl alcohol)Absolute configuration: (1R,2R)
