scholarly journals Reversible Hydrogen Transfer Reactions of Cysteine Thiyl Radicals in Peptides: the Conversion of Cysteine into Dehydroalanine and Alanine, and of Alanine into Dehydroalanine

2011 ◽  
Vol 115 (42) ◽  
pp. 12287-12305 ◽  
Author(s):  
Olivier Mozziconacci ◽  
Bruce A. Kerwin ◽  
Christian Schöneich
Keyword(s):  
Hydrogen Transfer ◽  
Transfer Reactions ◽  
Thiyl Radicals ◽  
Hydrogen Transfer Reactions

ChemInform Abstract: Intramolecular 1,2- and 1,3-Hydrogen Transfer Reactions of Thiyl Radicals

ChemInform ◽  
2014 ◽  
Vol 45 (23) ◽  
pp. no-no
Author(s):  
Christian Schoeneich ◽  
Olivier Mozziconacci ◽  
Willem H. Koppenol ◽  
Thomas Nauser
Keyword(s):  
Hydrogen Transfer ◽  
Transfer Reactions ◽  
Thiyl Radicals ◽  
Hydrogen Transfer Reactions

Intramolecular 1,2- and 1,3-Hydrogen Transfer Reactions of Thiyl Radicals

2014 ◽  
Vol 54 (3) ◽  
pp. 265-271 ◽  
Author(s):  
Christian Schöneich ◽  
Olivier Mozziconacci ◽  
Willem H. Koppenol ◽  
Thomas Nauser
Keyword(s):  
Hydrogen Transfer ◽  
Transfer Reactions ◽  
Thiyl Radicals ◽  
Hydrogen Transfer Reactions

scholarly journals Cysteine residues as catalysts for covalent peptide and protein modification: a role for thiyl radicals?

2011 ◽  
Vol 39 (5) ◽  
pp. 1254-1259 ◽  
Author(s):  
Christian Schöneich
Keyword(s):  
Oxidative Stress ◽  
Protein Modification ◽  
Hydrogen Transfer ◽  
Transfer Reactions ◽  
Hydrogen Deuterium Exchange ◽  
Amino Acid Residues ◽  
Thiyl Radicals ◽  
Hydrogen Deuterium ◽  
Intramolecular Hydrogen ◽  
Hydrogen Transfer Reactions

Cysteine thiyl radicals engage in reversible intramolecular hydrogen-transfer reactions with amino acid residues in peptides and proteins. These reactions can be experimentally demonstrated through covalent hydrogen–deuterium exchange when experiments are carried out in 2H2O. To this end, hydrogen-transfer reactions have been observed between cysteine thiyl radicals and glycine, alanine, serine, valine and leucine in both model peptides and a protein, insulin. The relevance of such reactions for protein oxidation under conditions of oxidative stress is discussed.

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