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Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction
Herein, we describe a synthetic strategy for the regioselective labeling of peptides by using a bioorthogonal click reaction between 2‐cyanobenzothiazole (CBT) and a 1,2‐aminothiol moiety. This methodology allows for the facile and site‐specific modification of peptides with various imaging agents,...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838389/ https://www.ncbi.nlm.nih.gov/pubmed/29531889 http://dx.doi.org/10.1002/open.201700191 |
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author | Chen, Kuo‐Ting Ieritano, Christian Seimbille, Yann |
author_facet | Chen, Kuo‐Ting Ieritano, Christian Seimbille, Yann |
author_sort | Chen, Kuo‐Ting |
collection | PubMed |
description | Herein, we describe a synthetic strategy for the regioselective labeling of peptides by using a bioorthogonal click reaction between 2‐cyanobenzothiazole (CBT) and a 1,2‐aminothiol moiety. This methodology allows for the facile and site‐specific modification of peptides with various imaging agents, including fluorophores and radioisotope‐containing prosthetic groups. We investigated the feasibility of an early‐stage incorporation of dipeptide 1 into targeting vectors, such as c[RGDyK(C)] and HER2 pep, during solid‐phase peptide synthesis. Then, the utility of the click reaction to label bioactive peptides with a CBT‐modified imaging agent (FITC–CBT, 9) was assessed. The ligation reaction was found to be highly selective and efficient under various conditions. The fluorescently labeled peptides 2 and 3 were obtained in respective yields of 88 and 82 % under optimized conditions. |
format | Online Article Text |
id | pubmed-5838389 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-58383892018-03-12 Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction Chen, Kuo‐Ting Ieritano, Christian Seimbille, Yann ChemistryOpen Communications Herein, we describe a synthetic strategy for the regioselective labeling of peptides by using a bioorthogonal click reaction between 2‐cyanobenzothiazole (CBT) and a 1,2‐aminothiol moiety. This methodology allows for the facile and site‐specific modification of peptides with various imaging agents, including fluorophores and radioisotope‐containing prosthetic groups. We investigated the feasibility of an early‐stage incorporation of dipeptide 1 into targeting vectors, such as c[RGDyK(C)] and HER2 pep, during solid‐phase peptide synthesis. Then, the utility of the click reaction to label bioactive peptides with a CBT‐modified imaging agent (FITC–CBT, 9) was assessed. The ligation reaction was found to be highly selective and efficient under various conditions. The fluorescently labeled peptides 2 and 3 were obtained in respective yields of 88 and 82 % under optimized conditions. John Wiley and Sons Inc. 2018-02-06 /pmc/articles/PMC5838389/ /pubmed/29531889 http://dx.doi.org/10.1002/open.201700191 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Communications Chen, Kuo‐Ting Ieritano, Christian Seimbille, Yann Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction |
title | Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction |
title_full | Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction |
title_fullStr | Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction |
title_full_unstemmed | Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction |
title_short | Early‐Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2‐Cyanobenzothiazole/1,2‐Aminothiol Bioorthogonal Click Reaction |
title_sort | early‐stage incorporation strategy for regioselective labeling of peptides using the 2‐cyanobenzothiazole/1,2‐aminothiol bioorthogonal click reaction |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838389/ https://www.ncbi.nlm.nih.gov/pubmed/29531889 http://dx.doi.org/10.1002/open.201700191 |
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