title: Conformationally constrained functional peptide monolayers for the controlled display of bioactive carbohydrate ligands.
abstract: In this study, we employed thiolated peptides of the conformationally constrained, strongly helicogenic α-aminoisobutyric acid (Aib) residue to prepare self-assembled monolayers (SAMs) on gold surfaces. Electrochemistry and infrared reflection absorption spectroscopy support the formation of very well packed Aib-peptide SAMs. The immobilized peptides retain their helical structure, and the resulting SAMs are stabilized by a network of intermolecular H bonds involving the NH groups adjacent to the Au surface. Binary SAMs containing a synthetically defined glycosylated mannose-functionalized Aib-peptide as the second component display similar features, thereby providing reproducible substrates suitable for the controlled display of bioactive carbohydrate ligands. The efficiency of such Aib-based SAMs as a biomolecular recognition platform was evidenced by examining the mannose-concanavalin A interaction via surface plasmon resonance biosensing.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania, United States.
authors.forename: Justin M
authors.initials: JM
authors.lastname: Kaplan
authors.forename: Jing
authors.initials: J
authors.lastname: Shang
authors.forename: Pierangelo
authors.initials: P
authors.lastname: Gobbo
authors.forename: Sabrina
authors.initials: S
authors.lastname: Antonello
authors.forename: Lidia
authors.initials: L
authors.lastname: Armelao
authors.forename: Vijay
authors.initials: V
authors.lastname: Chatare
authors.forename: Daniel M
authors.initials: DM
authors.lastname: Ratner
authors.forename: Rodrigo B
authors.initials: RB
authors.lastname: Andrade
authors.forename: Flavio
authors.initials: F
authors.lastname: Maran
mesh_terms: D000621:Aminoisobutyric Acids / Q000737:chemistry*; D003208:Concanavalin A / Q000032:analysis / Q000737:chemistry; D055664:Electrochemical Techniques; D006046:Gold / Q000737:chemistry*; D006860:Hydrogen Bonding; D055767:Immobilized Proteins / Q000138:chemical synthesis / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D055550:Protein Stability; D017433:Protein Structure, Secondary; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D020349:Surface Plasmon Resonance
chemical_list: D000621:Aminoisobutyric Acids; D055767:Immobilized Proteins; D010455:Peptides; D013438:Sulfhydryl Compounds; D003208:Concanavalin A; C100049:2-aminoisobutyric acid; D006046:Gold; D008358:Mannose