title: Reductive phosphine-mediated ligation of nitroxyl (HNO).
abstract: Nitroxyl (HNO) demonstrates a unique chemical and biological profile compared to nitric oxide (NO). Phosphorus NMR studies reveal that HNO reacts with triarylphosphines to give the corresponding phosphine oxide and aza-ylide. In the presence of a properly situated electrophilic ester, the aza-ylide undergoes a Staudinger ligation to yield an amide with the nitrogen atom being derived from HNO. These results define new HNO reactivity and provide the basis of new HNO detection methods.
authors.affiliation: Department of Chemistry, Salem Hall, Box 7486, Wake Forest University, Winston-Salem, North Carolina 27109, USA.
authors.forename: Julie A
authors.initials: JA
authors.lastname: Reisz
authors.forename: Erika B
authors.initials: EB
authors.lastname: Klorig
authors.forename: Marcus W
authors.initials: MW
authors.lastname: Wright
authors.forename: S Bruce
authors.initials: SB
authors.lastname: King
mesh_terms: D001372:Aza Compounds / Q000737:chemistry; D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009569:Nitric Oxide / Q000737:chemistry / Q000378:metabolism; D009589:Nitrogen Oxides / Q000032:analysis* / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*
chemical_list: D001372:Aza Compounds; D004952:Esters; D009589:Nitrogen Oxides; D010720:Phosphines; D009569:Nitric Oxide; C044646:phosphine; C039900:nitroxyl