Amino Acid–Viologen Hybrids: Synthesis, Cucurbituril Host–Guest Chemistry, and Implementation on the Production of Peptides

[Image: see text] We present herein the development of a series of viologen–amino acid hybrids, obtained in good yields either by successive alkylations of 4,4′-bipyridine, or by Zincke reactions followed by a second alkylation step. The potential of the obtained amino acids has been exemplified, ei...

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Autores principales: Barravecchia, Liliana, Neira, Iago, Pazos, Elena, Peinador, Carlos, García, Marcos D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8749954/
https://www.ncbi.nlm.nih.gov/pubmed/34889610
http://dx.doi.org/10.1021/acs.joc.1c02040
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author Barravecchia, Liliana
Neira, Iago
Pazos, Elena
Peinador, Carlos
García, Marcos D.
author_facet Barravecchia, Liliana
Neira, Iago
Pazos, Elena
Peinador, Carlos
García, Marcos D.
author_sort Barravecchia, Liliana
collection PubMed
description [Image: see text] We present herein the development of a series of viologen–amino acid hybrids, obtained in good yields either by successive alkylations of 4,4′-bipyridine, or by Zincke reactions followed by a second alkylation step. The potential of the obtained amino acids has been exemplified, either as typical guests of the curcubituril family of hosts (particularly CB[7]/[8]) or as suitable building blocks for the solution/solid-phase synthesis of two model tripeptides with the viologen core inserted within their sequences.
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spelling pubmed-87499542022-01-11 Amino Acid–Viologen Hybrids: Synthesis, Cucurbituril Host–Guest Chemistry, and Implementation on the Production of Peptides Barravecchia, Liliana Neira, Iago Pazos, Elena Peinador, Carlos García, Marcos D. J Org Chem [Image: see text] We present herein the development of a series of viologen–amino acid hybrids, obtained in good yields either by successive alkylations of 4,4′-bipyridine, or by Zincke reactions followed by a second alkylation step. The potential of the obtained amino acids has been exemplified, either as typical guests of the curcubituril family of hosts (particularly CB[7]/[8]) or as suitable building blocks for the solution/solid-phase synthesis of two model tripeptides with the viologen core inserted within their sequences. American Chemical Society 2021-12-10 2022-01-07 /pmc/articles/PMC8749954/ /pubmed/34889610 http://dx.doi.org/10.1021/acs.joc.1c02040 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Barravecchia, Liliana
Neira, Iago
Pazos, Elena
Peinador, Carlos
García, Marcos D.
Amino Acid–Viologen Hybrids: Synthesis, Cucurbituril Host–Guest Chemistry, and Implementation on the Production of Peptides
title Amino Acid–Viologen Hybrids: Synthesis, Cucurbituril Host–Guest Chemistry, and Implementation on the Production of Peptides
title_full Amino Acid–Viologen Hybrids: Synthesis, Cucurbituril Host–Guest Chemistry, and Implementation on the Production of Peptides
title_fullStr Amino Acid–Viologen Hybrids: Synthesis, Cucurbituril Host–Guest Chemistry, and Implementation on the Production of Peptides
title_full_unstemmed Amino Acid–Viologen Hybrids: Synthesis, Cucurbituril Host–Guest Chemistry, and Implementation on the Production of Peptides
title_short Amino Acid–Viologen Hybrids: Synthesis, Cucurbituril Host–Guest Chemistry, and Implementation on the Production of Peptides
title_sort amino acid–viologen hybrids: synthesis, cucurbituril host–guest chemistry, and implementation on the production of peptides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8749954/
https://www.ncbi.nlm.nih.gov/pubmed/34889610
http://dx.doi.org/10.1021/acs.joc.1c02040
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