title: Click to fit: versatile polyvalent display on a peptidomimetic scaffold.
abstract: We describe an efficient protocol to effect multisite conjugation reactions to oligomers on solid-phase support. Sequence-specific N-substituted glycine "oligopeptoids" were utilized as substrates for azide-alkyne cycloaddition reactions. Diverse groups, including nucleobases and fluorophores, were conjugated at up to six positions on peptoid side chains with yields ranging from 88 to 96%. This strategy will be broadly applicable for generating polyvalent displays on peptides and other scaffolds, allowing precise control of spacing between the displayed groups.
authors.affiliation: Department of Chemistry, New York University, New York, 10003-6688, USA.
authors.forename: Hangjun
authors.initials: H
authors.lastname: Jang
authors.forename: Aaron
authors.initials: A
authors.lastname: Fafarman
authors.forename: Justin M
authors.initials: JM
authors.lastname: Holub
authors.forename: Kent
authors.initials: K
authors.lastname: Kirshenbaum
mesh_terms: D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008958:Models, Molecular; D018716:Molecular Mimicry; D015394:Molecular Structure; D034444:Peptoids / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D034444:Peptoids; D005998:Glycine