Fit to be tied: Conformation-directed macrocyclization of peptoid foldamers

Justin M. Holub; Hangjun Jang; Kent Kirshenbaum

doi:10.1021/ol071169l

Fit to be tied: Conformation-directed macrocyclization of peptoid foldamers

Justin M. Holub, Hangjun Jang, Kent Kirshenbaum

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English (US)
Pages (from-to)	3275-3278
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	17
DOIs	https://doi.org/10.1021/ol071169l
State	Published - Aug 16 2007

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol071169l

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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.",

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AB - 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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Fit to be tied: Conformation-directed macrocyclization of peptoid foldamers

Abstract

ASJC Scopus subject areas

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