Reductive phosphine-mediated ligation of nitroxyl (HNO).
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.
Reisz
Julie A
JA
Department of Chemistry, Salem Hall, Box 7486, Wake Forest University, Winston-Salem, North Carolina 27109, USA.
Klorig
Erika B
EB
Wright
Marcus W
MW
King
S Bruce
SB
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*
D001372:Aza Compounds; D004952:Esters; D009589:Nitrogen Oxides; D010720:Phosphines; D009569:Nitric Oxide; C044646:phosphine; C039900:nitroxyl