Ultra-low temperature oxidation of 5,6-dihydroxyindole: a novel approach to study synthetic melanogenesis

Photochemistry and Photobiology
Lanying Q Hatcher, John D Simon

Abstract

The detailed structure of melanin remains elusive due to the complexity and insolubility of the pigment. Herein we describe a novel oxidation of 5,6-dihydroxyindole (DHI) as a means to characterize soluble intermediates formed prior to oligomerization. The approach entails the use of a biomimetic copper-peroxo oxidant, at ultra-low temperature (-78 degrees C). DHI oxidized by [LCuII(O2)CuIIL]B(C6F5)4 (L=2,6,10-trimethyl-2,6,10-triazaundecane) under argon produces the one electron oxidation product, semiquinone radical, which is spectroscopically observed at -78 degrees C. MS analysis of the reaction mixture reveals the DHI dimer as well as other extensively oxidized DHI units.

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Citations

Sep 23, 2011·Journal of Medicinal Chemistry·R G Waruna JinadasaKevin M Smith
Mar 19, 2009·Angewandte Chemie·Marco d'IschiaTadeusz Sarna
Aug 8, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shiori NakagawaMakoto Hashimoto

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