Synthesis of Chiral Scaffolds Based on Polyfunctional Cyclobutane β-Amino Acids

Chiral scaffolds have been synthesized through selective transformations from conveniently protected cyclobutane β-amino acids. The obtained derivatives present additional functional groups, such as hydroxyl, carboxyl, or carbon-carbon triple bond, linked to the amino acid core through a flexible C...

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Autores: Verkh, Yaroslav|||0000-0003-0258-505X, Illa, Ona|||0000-0001-7390-4893, Ortuño Mingarro, Rosa María|||0000-0001-7635-7354
Tipo de recurso: artículo
Fecha de publicación:2021
País:España
Institución:Universitat Autònoma de Barcelona
Repositorio:Dipòsit Digital de Documents de la UAB
Idioma:inglés
OAI Identifier:oai:ddd.uab.cat:251394
Acceso en línea:https://ddd.uab.cat/record/251394
https://dx.doi.org/urn:doi:10.1002/ejoc.202101192
Access Level:acceso abierto
Palabra clave:Aminoacids
Chiral scaffolds
Peptidomimetics
Polyfuctional chemical platforms
Unnatural peptides
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spelling Synthesis of Chiral Scaffolds Based on Polyfunctional Cyclobutane β-Amino AcidsVerkh, Yaroslav|||0000-0003-0258-505XIlla, Ona|||0000-0001-7390-4893Ortuño Mingarro, Rosa María|||0000-0001-7635-7354AminoacidsChiral scaffoldsPeptidomimeticsPolyfuctional chemical platformsUnnatural peptidesChiral scaffolds have been synthesized through selective transformations from conveniently protected cyclobutane β-amino acids. The obtained derivatives present additional functional groups, such as hydroxyl, carboxyl, or carbon-carbon triple bond, linked to the amino acid core through a flexible C or C alkyl fragment. The resultant molecules are highly versatile to be used as chiral precursors for the production of polyfunctional chemical platforms. These can be suitable for the synthesis of complex molecules, through condensation reactions, such as peptide coupling, dehydration between a carboxylic acid and an alcohol, or click chemistry. To illustrate some of these possibilities, two hybrid tripeptides have been prepared as examples of their synthetic potential. 22021-01-0120212021-01-01Articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://ddd.uab.cat/record/251394https://dx.doi.org/urn:doi:10.1002/ejoc.202101192reponame:Dipòsit Digital de Documents de la UABinstname:Universitat Autònoma de BarcelonaInglésengAgencia Estatal de Investigación https://doi.org/10.13039/501100011033 CTQ2016-77978-Ropen accesshttp://purl.org/coar/access_right/c_abf2Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, i la comunicació pública de l'obra, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original. No es permet la creació d'obres derivades.https://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:ddd.uab.cat:2513942026-06-06T12:50:31Z
dc.title.none.fl_str_mv Synthesis of Chiral Scaffolds Based on Polyfunctional Cyclobutane β-Amino Acids
title Synthesis of Chiral Scaffolds Based on Polyfunctional Cyclobutane β-Amino Acids
spellingShingle Synthesis of Chiral Scaffolds Based on Polyfunctional Cyclobutane β-Amino Acids
Verkh, Yaroslav|||0000-0003-0258-505X
Aminoacids
Chiral scaffolds
Peptidomimetics
Polyfuctional chemical platforms
Unnatural peptides
title_short Synthesis of Chiral Scaffolds Based on Polyfunctional Cyclobutane β-Amino Acids
title_full Synthesis of Chiral Scaffolds Based on Polyfunctional Cyclobutane β-Amino Acids
title_fullStr Synthesis of Chiral Scaffolds Based on Polyfunctional Cyclobutane β-Amino Acids
title_full_unstemmed Synthesis of Chiral Scaffolds Based on Polyfunctional Cyclobutane β-Amino Acids
title_sort Synthesis of Chiral Scaffolds Based on Polyfunctional Cyclobutane β-Amino Acids
dc.creator.none.fl_str_mv Verkh, Yaroslav|||0000-0003-0258-505X
Illa, Ona|||0000-0001-7390-4893
Ortuño Mingarro, Rosa María|||0000-0001-7635-7354
author Verkh, Yaroslav|||0000-0003-0258-505X
author_facet Verkh, Yaroslav|||0000-0003-0258-505X
Illa, Ona|||0000-0001-7390-4893
Ortuño Mingarro, Rosa María|||0000-0001-7635-7354
author_role author
author2 Illa, Ona|||0000-0001-7390-4893
Ortuño Mingarro, Rosa María|||0000-0001-7635-7354
author2_role author
author
dc.subject.none.fl_str_mv Aminoacids
Chiral scaffolds
Peptidomimetics
Polyfuctional chemical platforms
Unnatural peptides
topic Aminoacids
Chiral scaffolds
Peptidomimetics
Polyfuctional chemical platforms
Unnatural peptides
description Chiral scaffolds have been synthesized through selective transformations from conveniently protected cyclobutane β-amino acids. The obtained derivatives present additional functional groups, such as hydroxyl, carboxyl, or carbon-carbon triple bond, linked to the amino acid core through a flexible C or C alkyl fragment. The resultant molecules are highly versatile to be used as chiral precursors for the production of polyfunctional chemical platforms. These can be suitable for the synthesis of complex molecules, through condensation reactions, such as peptide coupling, dehydration between a carboxylic acid and an alcohol, or click chemistry. To illustrate some of these possibilities, two hybrid tripeptides have been prepared as examples of their synthetic potential.
publishDate 2021
dc.date.none.fl_str_mv 2
2021-01-01
2021
2021-01-01
dc.type.none.fl_str_mv Article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://ddd.uab.cat/record/251394
https://dx.doi.org/urn:doi:10.1002/ejoc.202101192
url https://ddd.uab.cat/record/251394
https://dx.doi.org/urn:doi:10.1002/ejoc.202101192
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 CTQ2016-77978-R
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
https://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Dipòsit Digital de Documents de la UAB
instname:Universitat Autònoma de Barcelona
instname_str Universitat Autònoma de Barcelona
reponame_str Dipòsit Digital de Documents de la UAB
collection Dipòsit Digital de Documents de la UAB
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