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• W1965057258 abstract "Abstract This paper summarizes our recent studies on the mechanism of O-atom transfer to a benzylic C–H bond promoted by dopamine β-hydroxylase (DBH) and its biomimetic models. We demonstrate that it is possible to carry out parallel and comparative studies on enzyme (DBH) and its biomimetic models with the same substrate: 2-aminoindane (1). It was chosen because its two stereogenic centers, both in benzylic positions, make it very powerful for studying the stereochemistry of an O-atom transfer reaction. DBH-catalyzed hydroxylation of 1 exclusively produced 14 % of trans-(1S,2S)-2-amino-1-indanol 4a (93 % e.e.). Studies with stereospecifically deuterium labeled 2-aminoindanes (1R,2S)-2 and (1S,2S)-3 showed that the formation of 4a was the result of an overall process with retention of configuration where an O-atom is stereospecifically inserted in the trans pro-S position of the substrate. Addition of 1 and (±)2 to 2-vinylpyridine gave 2-X-IndPY2 ligands 5 and 6, which were transformed into copper(I) and (II) complexes {7}(PF6) and {8}(CF3SO3), respectively. Reaction with dioxygen led to new complexes in which an O-atom transfer to a benzylic C–H bond has been performed in the same manner as that of DBH. With deuterium labeled cis-2-d-IndPY2 ligand 6, we demonstrated that the reaction occurs by a stereospecific process with retention of configuration. In both cases (enzymatic vs. biomimetic) the O-atom transfers occur in a two-step process involving radical intermediates." @default.
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• W1965057258 date "2001-01-01" @default.
• W1965057258 modified "2023-09-23" @default.
• W1965057258 title "Dopamine β-hydroxylase, a fascinating mammalian copper-containing monooxygenase: enzymatic and biomimetic studies of the O-atom transfer catalysis" @default.
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• W1965057258 doi "https://doi.org/10.1016/s1387-1609(00)01199-3" @default.
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