title: Chemoselectivity and the Chan-Lam Coupling Reaction: Adding Amino Acids to Polymer-Coated Microelectrode Arrays.
abstract: The placement of a peptide onto a microelectrode array is frequently complicated by the presence of multiple nucleophiles in the peptide. In the work reported here, we have found that the Chan-Lam coupling reactions used to site-selectively place thiol, alcohol, and amine nucleophiles onto diblock-copolymer-coated surfaces are chemoselective for the placement of thiol and alcohol nucleophiles on the arrays. This means that cysteine- and serine-containing peptides can be placed onto an array without any need to protect the N terminus of the peptide. Furthermore, it was found that placement of thiol groups onto an array with the Chan-Lam reaction using optimized reaction times leads to complete coverage of the electrodes. The extent of this coverage can be controlled by varying the reaction time in a manner that allows for the construction of arrays with a gradient of peptide concentrations.
authors.affiliation: Department of Chemistry, Washington University in St. Louis , St. Louis, Missouri 63130, United States.
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Graaf
authors.affiliation: Department of Chemistry, Washington University in St. Louis , St. Louis, Missouri 63130, United States.
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Moeller
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry*; D008839:Microelectrodes; D010455:Peptides / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D012694:Serine / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D010455:Peptides; D011108:Polymers; D012694:Serine; D003545:Cysteine