π-π Stacking Interaction in an Oxidized Cu -Salen Complex with a Side-Chain Indole Ring: An Approach to the Function of the Tryptophan in the Active Site of Galactose Oxidase.

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ID: 42707
2019
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Abstract
In order to gain new insights into the effect of the π-π stacking interaction of the indole ring with the Cu -phenoxyl radical as seen in the active form of galactose oxidase, we have prepared a Cu complex of a methoxy-substituted salen-type ligand, containing a pendent indole ring on the dinitrogen chelate backbone, and characterized its one-electron-oxidized forms. The X-ray crystal structures of the oxidized Cu complex exhibited the π-π stacking interaction of the indole ring mainly with one of the two phenolate moieties. The phenolate moiety in close contact with the indole moiety showed the characteristic phenoxyl radical structural features, indicating that the indole ring favors the π-π stacking interaction with the phenoxyl radical. The UV/Vis/NIR spectra of the oxidized Cu complex with the pendent indole ring was significantly different from those of the complex without the side-chain indole ring, and the absorption and CD spectra exhibited a solvent dependence, which is in line with the phenoxyl radical-indole stacking interaction in solution. The other physicochemical results and theoretical calculations strongly support that the indole ring, as an electron donor, stabilizes the phenoxyl radical by the π-π stacking interaction.
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oshita2019chemistry Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Oshita, Hiromi;Suzuki, Takashi;Kawashima, Kyohei;Abe, Hitoshi;Tani, Fumito;Mori, Seiji;Yajima, Tatsuo;Shimazaki, Yuichi;
Journal Chemistry (Weinheim an der Bergstrasse, Germany)
Year 2019
DOI
10.1002/chem.201900733
URL
Keywords
oxidation copper heterocycles radicals pi interactions

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