Introduction of the dansyl group into histidine and tyrosine residues in peptides and proteins.
Two dansyl derivatives: 1-(5-dimethylaminonaphthalene) sulfonyl (4-amino)-benzyl amine and 1-(5-dimethylaminonaphthalene) sulfonyl beta(4-aminophenyl) ethylamine, have been recently synthesized. Reaction of these compounds with nitrous acid lead to the corresponding dansyl-bearing diazonium salts. The latter derivatives can couple, under mild basic conditions, to the imidazole moiety of histidine, the phenolic ring of tyrosine and to the epsilon-amino function of lysine. The applicability of the two reagents was tested in the modification of several peptides, including [D-Phe6]LHRH, [D-Gln6]LHRH, Leu-enkephalin and Tyr-tuftsin, and proteins such as calmodulin, bovine serum albumin and nerve growth factor.
D055598:Chemical Phenomena; D002621:Chemistry; D003619:Dansyl Compounds; D006639:Histidine; D006863:Hydrogen-Ion Concentration; D010455:Peptides; D011506:Proteins; D013050:Spectrometry, Fluorescence; D013057:Spectrum Analysis; D014443:Tyrosine
D003619:Dansyl Compounds; D010455:Peptides; D011506:Proteins; D014443:Tyrosine; D006639:Histidine