Fit to be tied: conformation-directed macrocyclization of peptoid foldamers.
Covalent macrocyclic constraints can be readily installed on N-substituted glycine "peptoid" oligomer substrates. Cu(I)-catalyzed [3+2] cycloaddition reactions were conducted on solid support to ligate peptoid side chain azide and alkyne functionalities. Intramolecular macrocycle formation is facilitated by preorganizing the reactive groups across one turn of the helical secondary structure. These results confirm that conformational ordering can be exploited to assist the macrocyclization of folded oligomers.
Holub
Justin M
JM
Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003-6688, USA.
Jang
Hangjun
H
Kirshenbaum
Kent
K
D003500:Cyclization; D047028:Macrocyclic Compounds / Q000138:chemical synthesis; D008968:Molecular Conformation; D034444:Peptoids / Q000138:chemical synthesis* / Q000737:chemistry; D017433:Protein Structure, Secondary
D047028:Macrocyclic Compounds; D034444:Peptoids