Click to fit: versatile polyvalent display on a peptidomimetic scaffold.
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.
Jang
Hangjun
H
Department of Chemistry, New York University, New York, 10003-6688, USA.
Fafarman
Aaron
A
Holub
Justin M
JM
Kirshenbaum
Kent
K
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*
D034444:Peptoids; D005998:Glycine