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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Published inChemical communications (Cambridge, England) Vol. 52; no. 11; pp. 2334 - 2337
Main Authors Ramesh, Suhas, Cherkupally, Prabhakar, Govender, Thavendran, Kruger, Hendrik G., Albericio, Fernando, de la Torre, Beatriz G.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Amines - metabolism
Bromides
Bromine - metabolism
Chemical attack
Chemistry
Chemistry, Multidisciplinary
Magnetic Resonance Spectroscopy
Maleimides - metabolism
Peptides
Peptides - metabolism
Physical Sciences
Platforms
Proteins
Science & Technology
Sulfhydryl Compounds - metabolism
Vaccines
BIOCONJUGATION
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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.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc09457g