title: Templated alkylation of hexahistidine with Baylis-Hillman esters.
abstract: Alkylation of one of the imidazole rings of hexahistidine with Baylis-Hillman esters tethered to nitrilotriacetate residue was achieved in aqueous solutions at neutral pH and at micromolar concentrations in the presence of Ni(2+), Cu(2+), or Zn(2+) cations. The utility of the approach for selective functionalization of His-tagged recombinant proteins was demonstrated by attachment of a fluorescent label to recombinant protein A with an alkynyl group followed by a "click" 1,3-dipolar cycloaddition reaction.
authors.affiliation: Clarkson University, Department of Chemistry & Biomolecular Science, Potsdam, New York, USA. amelman@clarkson.edu.
authors.forename: Xing Xin
authors.initials: XX
authors.lastname: Liu
authors.forename: Artem
authors.initials: A
authors.lastname: Melman
mesh_terms: D000478:Alkylation; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D004952:Esters; D005456:Fluorescent Dyes / Q000737:chemistry; D006639:Histidine / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007093:Imidazoles / Q000737:chemistry; D007477:Ions / Q000737:chemistry; D009532:Nickel / Q000737:chemistry; D009842:Oligopeptides / Q000737:chemistry*; D011994:Recombinant Proteins / Q000096:biosynthesis / Q000737:chemistry / Q000235:genetics; D013205:Staphylococcal Protein A / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D014867:Water / Q000737:chemistry; D015032:Zinc / Q000737:chemistry
chemical_list: D004952:Esters; D005456:Fluorescent Dyes; C471213:His-His-His-His-His-His; D007093:Imidazoles; D007477:Ions; D009842:Oligopeptides; D011994:Recombinant Proteins; D013205:Staphylococcal Protein A; D014867:Water; D006639:Histidine; D003300:Copper; C029899:imidazole; D009532:Nickel; D015032:Zinc