Fit To Be Tied: Conformation-Directed Macrocyclization of Peptoid Foldamers
- 18 July 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (17) , 3275-3278
- https://doi.org/10.1021/ol071169l
Abstract
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.Keywords
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