Cargando…
Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design
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...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2012
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268209/ https://www.ncbi.nlm.nih.gov/pubmed/23095896 http://dx.doi.org/10.3390/molecules171112533 |
_version_ | 1783376234557734912 |
---|---|
author | Reinwarth, Michael Nasu, Daichi Kolmar, Harald Avrutina, Olga |
author_facet | Reinwarth, Michael Nasu, Daichi Kolmar, Harald Avrutina, Olga |
author_sort | Reinwarth, Michael |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-6268209 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62682092018-12-13 Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design Reinwarth, Michael Nasu, Daichi Kolmar, Harald Avrutina, Olga Molecules Review 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. MDPI 2012-10-24 /pmc/articles/PMC6268209/ /pubmed/23095896 http://dx.doi.org/10.3390/molecules171112533 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Review Reinwarth, Michael Nasu, Daichi Kolmar, Harald Avrutina, Olga Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design |
title | Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design |
title_full | Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design |
title_fullStr | Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design |
title_full_unstemmed | Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design |
title_short | Chemical Synthesis, Backbone Cyclization and Oxidative Folding of Cystine-knot Peptides — Promising Scaffolds for Applications in Drug Design |
title_sort | chemical synthesis, backbone cyclization and oxidative folding of cystine-knot peptides — promising scaffolds for applications in drug design |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268209/ https://www.ncbi.nlm.nih.gov/pubmed/23095896 http://dx.doi.org/10.3390/molecules171112533 |
work_keys_str_mv | AT reinwarthmichael chemicalsynthesisbackbonecyclizationandoxidativefoldingofcystineknotpeptidespromisingscaffoldsforapplicationsindrugdesign AT nasudaichi chemicalsynthesisbackbonecyclizationandoxidativefoldingofcystineknotpeptidespromisingscaffoldsforapplicationsindrugdesign AT kolmarharald chemicalsynthesisbackbonecyclizationandoxidativefoldingofcystineknotpeptidespromisingscaffoldsforapplicationsindrugdesign AT avrutinaolga chemicalsynthesisbackbonecyclizationandoxidativefoldingofcystineknotpeptidespromisingscaffoldsforapplicationsindrugdesign |