Journal
ORGANIC LETTERS
Volume 9, Issue 17, Pages 3275-3278Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol071169l
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- NCRR NIH HHS [C06RR-165720] Funding Source: Medline
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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.
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