Highly chemoselective ligation of thiol- and amino-peptides on a bromomaleimide core

Application of a bromomaleimide core allows for the incorporation of three different peptides. The key reactions of the process are the selective stapling of both thiol- and amino-peptides on two different sites of the core. The thiol-peptide attacks and replaces the bromide whereas the amino-peptid...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (11), p.2334-2337
Main Authors: Ramesh, Suhas, Cherkupally, Prabhakar, Govender, Thavendran, Kruger, Hendrik G, Albericio, Fernando, de la Torre, Beatriz G
Format: Article
Language:English
Subjects:
Amines - metabolism
Bromides
Bromine - metabolism
Chemical attack
Magnetic Resonance Spectroscopy
Maleimides - metabolism
Peptides
Peptides - metabolism
Platforms
Proteins
Sulfhydryl Compounds - metabolism
Vaccines
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Summary:Application of a bromomaleimide core allows for the incorporation of three different peptides. The key reactions of the process are the selective stapling of both thiol- and amino-peptides on two different sites of the core. The thiol-peptide attacks and replaces the bromide whereas the amino-peptide attaches to the ene-position of the core revealing differential and selective reactivity. This platform will have further application in protein chemistry, multidrug presentation and vaccine preparation. Application of a bromomaleimide core allows for the incorporation of three different peptides.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc09457g