Solid-phase synthesis of peptides containing 1-Hydroxypyridine-2-one (1,2-HOPO)

Herein a friendly method for the preparation of 1-hydroxypyridine-2-one (1,2-HOPO)-containing peptides is described. The elongation of the peptide is carried out on a solid support, using a protecting group for the ε-amino of the Lys that is removable in very mild conditions and that does not provok...

Full description

Bibliographic Details
Authors: Al Shaer, Danah, Albericio, Fernando, de la Torre, Beatriz G.
Format: article
Status:Versión aceptada para publicación
Publication Date:2020
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/239273
Online Access:http://hdl.handle.net/10261/239273
Access Level:Open access
id ES_1e1a2b66c31b543c8d4feb4cbd24eb6d
oai_identifier_str oai:digital.csic.es:10261/239273
network_acronym_str ES
network_name_str España
repository_id_str
spelling Solid-phase synthesis of peptides containing 1-Hydroxypyridine-2-one (1,2-HOPO)Al Shaer, DanahAlbericio, Fernandode la Torre, Beatriz G.Herein a friendly method for the preparation of 1-hydroxypyridine-2-one (1,2-HOPO)-containing peptides is described. The elongation of the peptide is carried out on a solid support, using a protecting group for the ε-amino of the Lys that is removable in very mild conditions and that does not provoke cleavage of the peptide from the resin. Once the ε-amino of the Lys is released, HOPO can be incorporated using a commercially available derivative (1,2-HOPO-4-COOH), which has a carboxylic acid at position 4 of the aromatic ring. 1,2-HOPO-4-COOH can be introduced with the free N-hydroxyl or protected with the benzyl group. The former is recommended in many cases. If the protected derivative is to be used, the benzyl group can be removed during global deprotection and cleavage from the resin by adding trifluoromethanesulfonic acid to the cleavage cocktail.The work was funded in part by the following: the National Research Foundation, South Africa (NRF) (# 105892 and Blue Sky’s Research Programme # 120386) and the University of KwaZulu-Natal (South Africa); and the Spanish Ministry of Science, Innovation, and Universities (RTI2018-093831-B-100), the Generalitat de Catalunya (2017 SGR 1439) (Spain), and Marató TV3 foundation 2018 (#20183530). We thank Professor Miquel Viñas (University of Barcelona) for fruitful discussions.ElsevierConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2021202120202021info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/239273reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttp://dx.doi.org/10.1016/j.tetlet.2020.152299Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2392732026-05-22T06:33:51Z
dc.title.none.fl_str_mv Solid-phase synthesis of peptides containing 1-Hydroxypyridine-2-one (1,2-HOPO)
title Solid-phase synthesis of peptides containing 1-Hydroxypyridine-2-one (1,2-HOPO)
spellingShingle Solid-phase synthesis of peptides containing 1-Hydroxypyridine-2-one (1,2-HOPO)
Al Shaer, Danah
title_short Solid-phase synthesis of peptides containing 1-Hydroxypyridine-2-one (1,2-HOPO)
title_full Solid-phase synthesis of peptides containing 1-Hydroxypyridine-2-one (1,2-HOPO)
title_fullStr Solid-phase synthesis of peptides containing 1-Hydroxypyridine-2-one (1,2-HOPO)
title_full_unstemmed Solid-phase synthesis of peptides containing 1-Hydroxypyridine-2-one (1,2-HOPO)
title_sort Solid-phase synthesis of peptides containing 1-Hydroxypyridine-2-one (1,2-HOPO)
dc.creator.none.fl_str_mv Al Shaer, Danah
Albericio, Fernando
de la Torre, Beatriz G.
author Al Shaer, Danah
author_facet Al Shaer, Danah
Albericio, Fernando
de la Torre, Beatriz G.
author_role author
author2 Albericio, Fernando
de la Torre, Beatriz G.
author2_role author
author
dc.contributor.none.fl_str_mv Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
description Herein a friendly method for the preparation of 1-hydroxypyridine-2-one (1,2-HOPO)-containing peptides is described. The elongation of the peptide is carried out on a solid support, using a protecting group for the ε-amino of the Lys that is removable in very mild conditions and that does not provoke cleavage of the peptide from the resin. Once the ε-amino of the Lys is released, HOPO can be incorporated using a commercially available derivative (1,2-HOPO-4-COOH), which has a carboxylic acid at position 4 of the aromatic ring. 1,2-HOPO-4-COOH can be introduced with the free N-hydroxyl or protected with the benzyl group. The former is recommended in many cases. If the protected derivative is to be used, the benzyl group can be removed during global deprotection and cleavage from the resin by adding trifluoromethanesulfonic acid to the cleavage cocktail.
publishDate 2020
dc.date.none.fl_str_mv 2020
2021
2021
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/239273
url http://hdl.handle.net/10261/239273
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv http://dx.doi.org/10.1016/j.tetlet.2020.152299
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869404317261234176
score 15.812455

Similar Items