Preorganised Dipeptide Mimics as Foldamer Building Blocks

Preorganised dipeptide mimics containing a 3,4‐disubstituted oxazolidin‐2‐one, a flexible methylene group, and a 1,4‐disubstituted triazole have been prepared in a few steps and high yield by copper‐catalysed azide–alkyne cycloaddition (CuAAC). The combination of these three moieties allows the form...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-06, Vol.2013 (17), p.3567-3573
Main Authors: Castellucci, Nicola, Tomasini, Claudia
Format: Article
Language:English
Subjects:
Click chemistry
Conformation analysis
Foldamers
Heterocycles
Peptidomimetics
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Summary:Preorganised dipeptide mimics containing a 3,4‐disubstituted oxazolidin‐2‐one, a flexible methylene group, and a 1,4‐disubstituted triazole have been prepared in a few steps and high yield by copper‐catalysed azide–alkyne cycloaddition (CuAAC). The combination of these three moieties allows the formation of a new dipeptide mimic that favours the formation of bent conformations, as we could demonstrate by IR and ROESY analysis. Rigid, flexible, rigid: the combination of a 3,4‐disubstituted oxazolidin‐2‐one ring, a flexible methylene group and a 1,4‐disubstituted triazole ring allows the formation of a new dipeptide mimic that favours the formation of bent conformations.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300194