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Molecules 2012, 17(11), 12533-12552; doi:10.3390/molecules171112533
Review

Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design

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Received: 15 August 2012; in revised form: 19 September 2012 / Accepted: 22 October 2012 / Published: 24 October 2012
(This article belongs to the Special Issue Chemical Protein and Peptide Synthesis)
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Abstract: Cystine-knot peptides display exceptional structural, thermal, and biological stability. Their eponymous motif consists of six cysteine residues that form three disulfide bonds, resulting in a notably rigid structural core. Since they highly tolerate either rational or combinatorial changes in their primary structure, cystine knots are considered to be promising frameworks for the development of peptide-based pharmaceuticals. Despite their relatively small size (two to three dozens amino acid residues), the chemical synthesis route is challenging since it involves critical steps such as head-to-tail cyclization and oxidative folding towards the respective bioactive isomer. Herein we describe the topology of cystine-knot peptides, their synthetic availability and briefly discuss potential applications of engineered variants in diagnostics and therapy.
Keywords: CCK; cyclotide; cystine knot; ICK; inhibitor; knottin; miniprotein; native chemical ligation; oxidative folding CCK; cyclotide; cystine knot; ICK; inhibitor; knottin; miniprotein; native chemical ligation; oxidative folding
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Reinwarth, M.; Nasu, D.; Kolmar, H.; Avrutina, O. Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design. Molecules 2012, 17, 12533-12552.

AMA Style

Reinwarth M, Nasu D, Kolmar H, Avrutina O. Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design. Molecules. 2012; 17(11):12533-12552.

Chicago/Turabian Style

Reinwarth, Michael; Nasu, Daichi; Kolmar, Harald; Avrutina, Olga. 2012. "Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design." Molecules 17, no. 11: 12533-12552.


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