title: Water compatible photoarylation of amino acids and peptides.
abstract: A novel photoarylation of amino acids and peptides is described, which tolerates the presence of water. Irradiation of Boc-protected amino acids in the presence of N-protected 2-azidobenzimidazoles leads to selective arylation of carboxy termini or side chains. The new reaction also works for peptides. Irradiation of the nonapeptide H-SPSYVYHQF-OH also resulted in selective arylation of the tyrosine side chains, as indicated by ESI-MS/MS fragmentation. Chemo- and regioselectivity could add the title reaction to the repertoire of photoaffinity labeling methods.
authors.affiliation: Institute of Organic Chemistry, TU Braunschweig, Hagenring 30, 38106 Braunschweig (Germany), Fax: (+49) 531-391-7744.
authors.forename: Alex
authors.initials: A
authors.lastname: Sudakow
authors.forename: Uli
authors.initials: U
authors.lastname: Papke
authors.forename: Thomas
authors.initials: T
authors.lastname: Lindel
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D001562:Benzimidazoles / Q000737:chemistry*; D007097:Imines / Q000737:chemistry; D010455:Peptides / Q000737:chemistry*; D055668:Photochemical Processes; D014867:Water / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D001562:Benzimidazoles; D007097:Imines; D010455:Peptides; D014867:Water; C017621:phenylnitrene
keywords: arylation; bioorthogonal reactions; nitrenes; peptides; photochemistry