Literature DB >> 33595752

Room temperature stable multitalent: highly reactive and versatile copper guanidine complexes in oxygenation reactions.

Melanie Paul1, Alexander Hoffmann1, Sonja Herres-Pawlis2.   

Abstract

Inspired by the efficiency of natural enzymes in organic transformation reactions, the development of synthetic catalysts for oxygenation and oxidation reactions under mild conditions still remains challenging. Tyrosinases serve as archetype when it comes to hydroxylation reactions involving molecular oxygen. We herein present new copper(I) guanidine halide complexes, capable of the activation of molecular oxygen at room temperature. The formation of the reactive bis(µ-oxido) dicopper(III) species and the influence of the anion are investigated by UV/Vis spectroscopy, mass spectrometry, and density functional theory. We highlight the catalytic hydroxylation activity towards diverse polycyclic aromatic alcohols under mild reaction conditions. The selective formation of reactive quinones provides a promising tool to design phenazine derivatives for medical applications.

Entities:  

Keywords:  Copper catalysis; Dioxygen activation; Guanidine; Phenazine; Tyrosinase

Year:  2021        PMID: 33595752     DOI: 10.1007/s00775-021-01849-9

Source DB:  PubMed          Journal:  J Biol Inorg Chem        ISSN: 0949-8257            Impact factor:   3.358


  33 in total

Review 1.  Structure and spectroscopy of copper-dioxygen complexes.

Authors:  Liviu M Mirica; Xavier Ottenwaelder; T Daniel P Stack
Journal:  Chem Rev       Date:  2004-02       Impact factor: 60.622

2.  Overcoming the "oxidant problem": strategies to use O2 as the oxidant in organometallic C-H oxidation reactions catalyzed by Pd (and Cu).

Authors:  Alison N Campbell; Shannon S Stahl
Journal:  Acc Chem Res       Date:  2012-01-23       Impact factor: 22.384

3.  Action of tyrosinase on ortho-substituted phenols: possible influence on browning and melanogenesis.

Authors:  Maria del Mar Garcia-Molina; Jose Luis Muñoz-Muñoz; Francisco Garcia-Molina; Pedro Antonio García-Ruiz; Francisco Garcia-Canovas
Journal:  J Agric Food Chem       Date:  2012-06-18       Impact factor: 5.279

4.  Catalytic aerobic oxidation of phenols to ortho-quinones with air-stable copper precatalysts.

Authors:  M S Askari; L A Rodríguez-Solano; A Proppe; B McAllister; J-P Lumb; X Ottenwaelder
Journal:  Dalton Trans       Date:  2015-07-21       Impact factor: 4.390

Review 5.  Copper active sites in biology.

Authors:  Edward I Solomon; David E Heppner; Esther M Johnston; Jake W Ginsbach; Jordi Cirera; Munzarin Qayyum; Matthew T Kieber-Emmons; Christian H Kjaergaard; Ryan G Hadt; Li Tian
Journal:  Chem Rev       Date:  2014-03-03       Impact factor: 60.622

Review 6.  Copper-Oxygen Complexes Revisited: Structures, Spectroscopy, and Reactivity.

Authors:  Courtney E Elwell; Nicole L Gagnon; Benjamin D Neisen; Debanjan Dhar; Andrew D Spaeth; Gereon M Yee; William B Tolman
Journal:  Chem Rev       Date:  2017-01-19       Impact factor: 60.622

7.  Copper-Catalyzed Aerobic Oxidations of Organic Molecules: Pathways for Two-Electron Oxidation with a Four-Electron Oxidant and a One-Electron Redox-Active Catalyst.

Authors:  Scott D McCann; Shannon S Stahl
Journal:  Acc Chem Res       Date:  2015-05-28       Impact factor: 22.384

8.  N-acetyl-L-tyrosine (NAT) as a substrate for mushroom tyrosinase.

Authors:  V Kahn; N Ben-Shalom
Journal:  Pigment Cell Res       Date:  1998-02

9.  Tyrosinase and catechol oxidase activity of copper(I) complexes supported by imidazole-based ligands: structure-reactivity correlations.

Authors:  Franziska Wendt; Christian Näther; Felix Tuczek
Journal:  J Biol Inorg Chem       Date:  2016-06-22       Impact factor: 3.358

10.  Living with Oxygen.

Authors:  Harry B Gray; Jay R Winkler
Journal:  Acc Chem Res       Date:  2018-07-17       Impact factor: 22.384

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