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

Journal of Peptide Science : an Official Publication of the European Peptide Society
P R WerkhovenRob M J Liskamp

Abstract

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.

References

May 6, 2004·Journal of the American Chemical Society·Didier BoturynPascal Dumy
Apr 7, 2005·Chembiochem : a European Journal of Chemical Biology·Peter TimmermanRob H Meloen
Aug 8, 2006·Chembiochem : a European Journal of Chemical Biology·Yashveer SinghPascal Dumy
Sep 1, 2012·Chemical Communications : Chem Comm·Gwenn E MulderRob M J Liskamp
Mar 8, 2013·Organic & Biomolecular Chemistry·Gwenn E MulderRob M J Liskamp

Citations

Dec 17, 2016·Chembiochem : a European Journal of Chemical Biology·Helmus van de LangemheenRob M J Liskamp
Sep 16, 2020·Chemical Communications : Chem Comm·Jacky C H ChuDennis K P Ng
Feb 15, 2020·Chemical Science·Rhiannon BeardEdward W Tate
Jan 28, 2020·Journal of Peptide Science : an Official Publication of the European Peptide Society·Theodorus J MeulemanRob M J Liskamp
Oct 5, 2016·Biopolymers·Jordan M AndersonNiels H Andersen
Oct 24, 2020·Chemical Communications : Chem Comm·Norikazu TerashimaSuguru Yoshida
Nov 27, 2020·Chemical Communications : Chem Comm·Hinano TakemuraSuguru Yoshida
Dec 29, 2020·Chemical Communications : Chem Comm·Suguru YoshidaTakamitsu Hosoya

Related Concepts

Bordetella pertussis outer membrane protein P69
Alkynes
Azides
Outer Membrane Lipoproteins, Bacterial
Bordetella pertussis Bacterium
Copper
Cyclic Peptides
Agglutinogen 2, Bordetella Pertussis
Molecular Mimicry
Spectrometry, Mass, Electrospray Ionization

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