Diruthenium Diacetate Catalysed Aerobic Oxidation of Hydroxylamines and Improved Chemoselectivity by Immobilisation to Lysozyme
Flavia Lupi
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
LENS, University of Florence, Via Nello Carrara 1, 50019 Sesto Fiorentino (FI), Italy
Search for more papers by this authorDr. Tiziano Marzo
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
Dipartimento di Chimica e Chimica Industriale (DCCI), Università di Pisa, Via Moruzzi, 13, 56124 Pisa, Italy
These Authors contributed equally to this work.
Search for more papers by this authorDr. Giampiero D'Adamio
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
These Authors contributed equally to this work.
Search for more papers by this authorSara Cretella
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
Search for more papers by this authorCorresponding Author
Prof. Francesca Cardona
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
Associated with CNR-INO, Via Nello Carrara 1, Sesto Fiorentino (FI), Italy
Search for more papers by this authorCorresponding Author
Prof. Luigi Messori
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
Search for more papers by this authorCorresponding Author
Prof. Andrea Goti
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
Associated with CNR-INO, Via Nello Carrara 1, Sesto Fiorentino (FI), Italy
Search for more papers by this authorFlavia Lupi
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
LENS, University of Florence, Via Nello Carrara 1, 50019 Sesto Fiorentino (FI), Italy
Search for more papers by this authorDr. Tiziano Marzo
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
Dipartimento di Chimica e Chimica Industriale (DCCI), Università di Pisa, Via Moruzzi, 13, 56124 Pisa, Italy
These Authors contributed equally to this work.
Search for more papers by this authorDr. Giampiero D'Adamio
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
These Authors contributed equally to this work.
Search for more papers by this authorSara Cretella
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
Search for more papers by this authorCorresponding Author
Prof. Francesca Cardona
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
Associated with CNR-INO, Via Nello Carrara 1, Sesto Fiorentino (FI), Italy
Search for more papers by this authorCorresponding Author
Prof. Luigi Messori
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
Search for more papers by this authorCorresponding Author
Prof. Andrea Goti
Dipartimento di Chimica “Ugo Schiff”, Università di Firenze, Via della Lastruccia 3–13, 50019 Sesto Fiorentino (FI), Italy
Associated with CNR-INO, Via Nello Carrara 1, Sesto Fiorentino (FI), Italy
Search for more papers by this authorGraphical Abstract
Lysozyme support: The novel aerobic oxidation of hydroxylamines to nitrones catalyzed by Ru2(OAc)4Cl or its adduct with lysozyme [HEWL/Ru2(OAc)2] is reported. The coordination of the diruthenium moiety to the protein imparts complete chemoselectivity to the reaction, in contrast to the metallic complex alone.
Abstract
A new green method for the preparation of nitrones through the aerobic oxidation of the corresponding N,N-disubstituted hydroxylamines has been developed upon exploring the catalytic activity of a diruthenium catalyst, that is, [Ru2(OAc)4Cl]), in aqueous or alcoholic solution under mild reaction conditions (0.1 to 1 mol % catalyst, air, 50 °C) and reasonable reaction times. Notably, the catalytic activity of the dimetallic centre is retained after its binding to the small protein lysozyme. Interestingly, this new artificial metalloenzyme conferred complete chemoselectivity to the oxidation of cyclic hydroxylamines, in contrast to the diruthenium catalyst.
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