Beilstein J. Org. Chem.2017,13, 2428–2441, doi:10.3762/bjoc.13.240
groups is accessible for the use as precursors of peptidomimetics.
Keywords: amino acid analogous side chains; desilylation; Ellman’s chiral sulfinamide; intramolecularHuisgenreaction; peptidomimetics; propargylamines; rearrangement to α,β-unsaturated imines; Introduction
Terminal alkynes display an
14w have been successfully applied as inhibitors of β-glucosidases [107] and hexosamidases [108], this intramolecularHuisgenreaction could be exploited to develop novel enzyme inhibitors.
In order to get access to propargylamines with the side chains of lysine, ornithine and arginine, azide 7wx
side chain can be introduced using masked or protected functionalities. Side chains with amino groups were introduced masked as azide. For this purpose, the unprecedented intramolecularHuisgenreaction has to be suppressed. Electron-withdrawing substituents in the Cβ-position could not be used by this
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Graphical Abstract
Figure 1:
Concept of carboxylic acid or amide bond replacement on the basis of an alkyne moiety.