The tert-Butyl Side Chain: A Powerful Means to Lock Peptoid Amide Bonds in the Cis Conformation

The tert-Butyl Side Chain: A Powerful Means to Lock Peptoid Amide Bonds in the Cis Conformation

The very simple sterically hindered tert-butyl side chain exerts complete control over the peptoid amide geometry which only exists in the cis conformation. It is exemplified in NtBu glycine homo-oligomers and in linear oligopeptoids designed with an alternating cis–trans backbone amide pattern.

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Veröffentlicht in:Organic letters 2013-05, Vol.15 (9), p.2246-2249
Hauptverfasser: Roy, O, Caumes, C, Esvan, Y, Didierjean, C, Faure, S, Taillefumier, C
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Chemical Sciences
Cristallography
Crystallography, X-Ray
Glycine - chemistry
Models, Molecular
Molecular Conformation
Oligopeptides - chemistry
Peptoids - chemistry
Stereoisomerism
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Zusammenfassung:The very simple sterically hindered tert-butyl side chain exerts complete control over the peptoid amide geometry which only exists in the cis conformation. It is exemplified in NtBu glycine homo-oligomers and in linear oligopeptoids designed with an alternating cis–trans backbone amide pattern.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400820y