Journal
NEW JOURNAL OF CHEMISTRY
Volume 25, Issue 1, Pages 116-124Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b006545p
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A series of substituted arenes containing remote chiral centers were screened as substrates for toluene dioxygenase (TDO). The absolute stereochemistry of the new metabolites was determined by chemical and spectroscopic correlation with synthetic standards. There was no evidence for kinetic resolution; enantiomers were indiscriminately processed by the enzyme to diastereomeric pairs, which were separable upon derivatization. Some of these new metabolites are useful as synthons for morphine synthesis. Full experimental details are reported for those new compounds stable to isolation and for derivatives of those that are unstable.
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