Format:
Online-Ressource
ISSN:
1521-3773
Content:
Abstract: The ability to modify peptides and proteins chemoselectively is of continued interest in medicinal chemistry, with peptide conjugation, lipidation, stapling, and disulfide engineering at the forefront of modern peptide chemistry. Herein we report a robust method for the on‐resin preparation of allenamide‐modified peptides, an unexplored functionality for peptides that provides a versatile chemical tool for chemoselective inter‐ or intramolecular bridging reactions with thiols. The bridging reaction is biocompatible, occurring spontaneously at pH 7.4 in catalyst‐free aqueous media. By this “click” approach, a model peptide was successfully modified with a diverse range of alkyl and aryl thiols. Furthermore, this technique was demonstrated as a valuable tool to induce spontaneous intramolecular cyclisation by preparation of an oxytocin analogue, in which the native disulfide bridge was replaced with a vinyl sulfide moiety formed by thia‐Michael addition of a cysteine thiol to the allenamide handle.
In:
volume:59
In:
number:41
In:
year:2020
In:
pages:18054-18061
In:
extent:8
In:
Angewandte Chemie / International edition, Weinheim : Wiley-VCH, 1962-, 59, Heft 41 (2020), 18054-18061 (gesamt 8), 1521-3773
Language:
English
DOI:
10.1002/anie.202004656
URN:
urn:nbn:de:101:1-2022061409072685344029
URL:
https://doi.org/10.1002/anie.202004656
URL:
https://nbn-resolving.org/urn:nbn:de:101:1-2022061409072685344029
URL:
https://d-nb.info/1259812065/34
URL:
https://doi.org/10.1002/anie.202004656
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