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Versatile convergent synthesis of a three peptide loop containing protein mimic of whooping cough pertactin by successive Cu(I)‐catalyzed azide alkyne cycloaddition on an orthogonal alkyne functionalized TAC‐scaffold
Author(s) -
Werkhoven Paul R.,
Langemheen Helmus,
Wal Steffen,
Kruijtzer John A. W.,
Liskamp Rob M. J.
Publication year - 2014
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.2624
Subject(s) - cycloaddition , alkyne , peptide , azide , combinatorial chemistry , peptide library , chemistry , peptide synthesis , click chemistry , catalysis , biochemistry , organic chemistry , peptide sequence , gene
Synthetic mimics of discontinuous epitopes may have a wide range of potential applications, including synthetic vaccines and inhibition of protein–protein interactions. However, synthetic access to these relatively complex peptide molecular constructs is limited. This paper describes a versatile convergent strategy for the construction of protein mimics presenting three different cyclic peptides. Using an orthogonal alkyne protection strategy, peptide loops were introduced successively onto a triazacyclophane scaffold via Cu(I)‐catalyzed azide alkyne cycloaddition. This method provides rapid access to protein mimics requiring different peptide segments for their interaction and activity. Copyright © 2014 European Peptide Society and John Wiley & Sons, Ltd.