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Five Nitrogen Oxidation States from Nitro to Amine: Stabilization and Reactivity of a Metastable Arylhydroxylamine Complex.

Author(s): Zsombor-Pindera J; Effaty F; Escomel L; Patrick B; Kennepohl P; Ottenwaelder X;

Redox noninnocent ligands enhance the reactivity of the metal they complex, a strategy used by metalloenzymes and in catalysis. Herein, we report a series of copper complexes with the same ligand framework, but with a pendant nitrogen group that spans five ...

Article GUID: 33124796
Scavenging with TEMPO* to identify peptide- and protein-based radicals by mass spectrometry: advantages of spin scavenging over spin trapping.

Author(s): Wright PJ, English AM

J Am Chem Soc. 2003 Jul 16;125(28):8655-65 Authors: Wright PJ, English AM

Article GUID: 12848573
Superoxide dismutase targets NO from GSNO to Cysbeta93 of oxyhemoglobin in concentrated but not dilute solutions of the protein.

Author(s): Romeo AA, Capobianco JA, English AM

J Am Chem Soc. 2003 Nov 26;125(47):14370-8 Authors: Romeo AA, Capobianco JA, English AM

Article GUID: 14624585
Lipid binding to the carotenoid binding site in photosynthetic reaction centers.

Author(s): Deshmukh SS, Tang K, Kálmán L

J Am Chem Soc. 2011 Oct 12;133(40):16309-16 Authors: Deshmukh SS, Tang K, Kálmán L

Article GUID: 21894992
LC-MS/MS Proteoform Profiling Exposes Cytochrome c Peroxidase Self-Oxidation in Mitochondria and Functionally Important Hole Hopping from Its Heme

Author(s): Kathiresan M; English AM;

LC-MS/MS profiling reveals that the proteoforms of cytochrome c peroxidase (Ccp1) isolated from respiring yeast mitochondria are oxidized at numerous Met, Trp, and Tyr residues. In vitro oxidation of recombinant Ccp1 by H2O2 in the absence of its reducing s...

Article GUID: 30145880
Title:Five Nitrogen Oxidation States from Nitro to Amine: Stabilization and Reactivity of a Metastable Arylhydroxylamine Complex.
Authors:Zsombor-Pindera J,  Effaty F,  Escomel L,  Patrick B,  Kennepohl P,  Ottenwaelder X, 
Link:https://www.ncbi.nlm.nih.gov/pubmed/33124796
DOI:10.1021/jacs.0c09300
Category:J Am Chem Soc
PMID:33124796
Dept Affiliation: CHEMBIOCHEM
1 Department of Chemistry and Biochemistry, Concordia University, Montreal, QC H4B 1R6, Canada.
2 Department of Chemistry, University of British Columbia, Vancouver, BC V6T 1Z1, Canada.

Description:

Redox noninnocent ligands enhance the reactivity of the metal they complex, a strategy used by metalloenzymes and in catalysis. Herein, we report a series of copper complexes with the same ligand framework, but with a pendant nitrogen group that spans five different redox states between nitro and amine. Of particular interest is the synthesis of a unprecedented copper(I)-arylhydroxylamine complex. While hydroxylamines typically disproportionate or decompose in the presence of transition metal ions, the reactivity of this metastable species is arrested by the presence of an intramolecular hydrogen bond. Two-electron oxidation yields a copper(II)-(arylnitrosyl radical) complex that can dissociate to a copper(I) species with uncoordinated arylnitroso. This combination of ligand redox noninnocence and hemilability provides opportunities in catalysis for two-electron chemistry via a one-electron copper(I/II) shuttle, as exemplified with an aerobic alcohol oxidation.

PMID: 33124796 [PubMed - as supplied by publisher]