Small Head-to-Tail Macrocyclic α-Peptoids | Zendy

Adrian S. Culf | Zendy; Miroslava ČuperlovićCulf | Zendy; D. Léger | Zendy; A. Decken | Zendy

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Small Head-to-Tail Macrocyclic α-Peptoids

Author(s) -

Adrian S. Culf,

Miroslava ČuperlovićCulf,

D. Léger,

A. Decken

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol501102b

Subject(s) - chemistry , head (geology) , combinatorial chemistry , stereochemistry , geology , geomorphology

A convenient and efficient methodology for the head-to-tail macrocyclization of small 3-mer, 4-mer, and 5-mer α-peptoid acids (9-, 12-, and 15-atom N-substituted glycine oligomers) is described. The cyclic trimer has a ccc amide sequence in the crystal structure, whereas the tetramer has ctct and the pentamer has ttccc stereochemistry. NMR analysis reveals rigid structures in solution. These synthetic macrocycles may prove useful in medicinal and materials applications.

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