title: Comparison of HNO reactivity with tryptophan and cysteine in small peptides.
abstract: Recent discoveries of important pharmacological properties have drawn attention to the reactivity of HNO (azanone, nitroxyl) with biologically relevant substrates. Apart from its role in thiol oxidation, HNO has been reported to have nitrosative properties, for example, with tryptophan resulting in N-nitrosotryptophan formation. We have investigated the reactivity of HNO with tryptophan and small peptides containing either tryptophan or both a tryptophan and a cysteine residue. Our results point to the more reactive nature of cysteine towards HNO compared with tryptophan.
authors: Department of Chemistry, Johns Hopkins University, Baltimore, MD 21218, United States.
authors: Gizem
authors: G
authors: Keceli
authors: Department of Chemistry, Johns Hopkins University, Baltimore, MD 21218, United States.
authors: Cathy D
authors: CD
authors: Moore
authors: Department of Chemistry, Johns Hopkins University, Baltimore, MD 21218, United States. Electronic address: jtoscano@jhu.edu.
authors: John P
authors: JP
authors: Toscano
mesh_terms: D003545:Cysteine / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D009589:Nitrogen Oxides; D010455:Peptides; D014364:Tryptophan; C039900:nitroxyl; D003545:Cysteine
keywords: Cysteine- and tryptophan-containing peptides; HNO; HNO-derived N-nitrosotryptophan