Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds

The chemical synthesis of peptide-based [1]rotaxanes (lasso peptides) was achieved by [2]rotaxane formation followed by two chemoselective ligation reactions. Our approach enabled incorporation of various peptide sequences into a common rotaxane structure. The synthetic lasso peptides were character...

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Detalles Bibliográficos
Autores principales: Saito, Fumito, Bode, Jeffrey W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5427998/
https://www.ncbi.nlm.nih.gov/pubmed/28553526
http://dx.doi.org/10.1039/c7sc00021a
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author Saito, Fumito
Bode, Jeffrey W.
author_facet Saito, Fumito
Bode, Jeffrey W.
author_sort Saito, Fumito
collection PubMed
description The chemical synthesis of peptide-based [1]rotaxanes (lasso peptides) was achieved by [2]rotaxane formation followed by two chemoselective ligation reactions. Our approach enabled incorporation of various peptide sequences into a common rotaxane structure. The synthetic lasso peptides were characterized by NMR, chromatography, and partial degradation by proteases. A linear peptide epitope grafted onto the rotaxane scaffold showed significantly improved proteolytic stability.
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spelling pubmed-54279982017-05-26 Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds Saito, Fumito Bode, Jeffrey W. Chem Sci Chemistry The chemical synthesis of peptide-based [1]rotaxanes (lasso peptides) was achieved by [2]rotaxane formation followed by two chemoselective ligation reactions. Our approach enabled incorporation of various peptide sequences into a common rotaxane structure. The synthetic lasso peptides were characterized by NMR, chromatography, and partial degradation by proteases. A linear peptide epitope grafted onto the rotaxane scaffold showed significantly improved proteolytic stability. Royal Society of Chemistry 2017-04-01 2017-01-26 /pmc/articles/PMC5427998/ /pubmed/28553526 http://dx.doi.org/10.1039/c7sc00021a Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Saito, Fumito
Bode, Jeffrey W.
Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds
title Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds
title_full Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds
title_fullStr Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds
title_full_unstemmed Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds
title_short Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds
title_sort synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5427998/
https://www.ncbi.nlm.nih.gov/pubmed/28553526
http://dx.doi.org/10.1039/c7sc00021a
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