Comparison of HNO reactivity with tryptophan and cysteine in small peptides

Gizem Keceli, Cathy D. Moore, John P. Toscano

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish (US)
Pages (from-to)3710-3713
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Issue number16
StatePublished - Aug 15 2014


  • Cysteine- and tryptophan-containing peptides
  • HNO
  • HNO-derived N-nitrosotryptophan

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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