Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives

Autores
Cristófalo, Alejandro Ezequiel; Cano, María Emilia; Uhrig, María Laura
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Carbohydrate-protein interactions are involved in a myriad of biological processes. Thus, glycomimetics have arisen as one of the most promising synthetic targets to that end. Within the broad variety of glycomimetics, thiodisaccharides have proven to be excellent tools to study these processes, and even more, some of them unveiled interesting biological activities. This review brings together research made on the introduction of N-acetylhexosamine residues into thiodisaccharides to date, passing through classic substitution (as SN2, thioglycosylation and ring-opening reactions) and addition (as thiol-ene coupling and Michael-type additions) reactions. Recent and interesting developments regarding addition reactions to vinyl azides, cross-coupling reactions and novel chemoenzymatic methods are also discussed.
Fil: Cristófalo, Alejandro Ezequiel. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Cano, María Emilia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Uhrig, María Laura. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Materia
BIOMIMETIC SYNTHESIS
GLYCOSYLATION
N-ACETYLGLUCOSAMINE
THIOGLYCOSIDES.
THIOSUGARS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/165532
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and PerspectivesCristófalo, Alejandro EzequielCano, María EmiliaUhrig, María LauraBIOMIMETIC SYNTHESISGLYCOSYLATIONN-ACETYLGLUCOSAMINETHIOGLYCOSIDES.THIOSUGARShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Carbohydrate-protein interactions are involved in a myriad of biological processes. Thus, glycomimetics have arisen as one of the most promising synthetic targets to that end. Within the broad variety of glycomimetics, thiodisaccharides have proven to be excellent tools to study these processes, and even more, some of them unveiled interesting biological activities. This review brings together research made on the introduction of N-acetylhexosamine residues into thiodisaccharides to date, passing through classic substitution (as SN2, thioglycosylation and ring-opening reactions) and addition (as thiol-ene coupling and Michael-type additions) reactions. Recent and interesting developments regarding addition reactions to vinyl azides, cross-coupling reactions and novel chemoenzymatic methods are also discussed.Fil: Cristófalo, Alejandro Ezequiel. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Cano, María Emilia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Uhrig, María Laura. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaJohn Wiley & Sons Inc.2021-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/165532Cristófalo, Alejandro Ezequiel; Cano, María Emilia; Uhrig, María Laura; Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives; John Wiley & Sons Inc.; Chemical Record; 21; 10; 6-2021; 2808-28361527-8999CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/tcr.202100146info:eu-repo/semantics/altIdentifier/doi/10.1002/tcr.202100146info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:55:49Zoai:ri.conicet.gov.ar:11336/165532instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:55:49.381CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives
title Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives
spellingShingle Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives
Cristófalo, Alejandro Ezequiel
BIOMIMETIC SYNTHESIS
GLYCOSYLATION
N-ACETYLGLUCOSAMINE
THIOGLYCOSIDES.
THIOSUGARS
title_short Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives
title_full Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives
title_fullStr Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives
title_full_unstemmed Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives
title_sort Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives
dc.creator.none.fl_str_mv Cristófalo, Alejandro Ezequiel
Cano, María Emilia
Uhrig, María Laura
author Cristófalo, Alejandro Ezequiel
author_facet Cristófalo, Alejandro Ezequiel
Cano, María Emilia
Uhrig, María Laura
author_role author
author2 Cano, María Emilia
Uhrig, María Laura
author2_role author
author
dc.subject.none.fl_str_mv BIOMIMETIC SYNTHESIS
GLYCOSYLATION
N-ACETYLGLUCOSAMINE
THIOGLYCOSIDES.
THIOSUGARS
topic BIOMIMETIC SYNTHESIS
GLYCOSYLATION
N-ACETYLGLUCOSAMINE
THIOGLYCOSIDES.
THIOSUGARS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Carbohydrate-protein interactions are involved in a myriad of biological processes. Thus, glycomimetics have arisen as one of the most promising synthetic targets to that end. Within the broad variety of glycomimetics, thiodisaccharides have proven to be excellent tools to study these processes, and even more, some of them unveiled interesting biological activities. This review brings together research made on the introduction of N-acetylhexosamine residues into thiodisaccharides to date, passing through classic substitution (as SN2, thioglycosylation and ring-opening reactions) and addition (as thiol-ene coupling and Michael-type additions) reactions. Recent and interesting developments regarding addition reactions to vinyl azides, cross-coupling reactions and novel chemoenzymatic methods are also discussed.
Fil: Cristófalo, Alejandro Ezequiel. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Cano, María Emilia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Uhrig, María Laura. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
description Carbohydrate-protein interactions are involved in a myriad of biological processes. Thus, glycomimetics have arisen as one of the most promising synthetic targets to that end. Within the broad variety of glycomimetics, thiodisaccharides have proven to be excellent tools to study these processes, and even more, some of them unveiled interesting biological activities. This review brings together research made on the introduction of N-acetylhexosamine residues into thiodisaccharides to date, passing through classic substitution (as SN2, thioglycosylation and ring-opening reactions) and addition (as thiol-ene coupling and Michael-type additions) reactions. Recent and interesting developments regarding addition reactions to vinyl azides, cross-coupling reactions and novel chemoenzymatic methods are also discussed.
publishDate 2021
dc.date.none.fl_str_mv 2021-06
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/165532
Cristófalo, Alejandro Ezequiel; Cano, María Emilia; Uhrig, María Laura; Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives; John Wiley & Sons Inc.; Chemical Record; 21; 10; 6-2021; 2808-2836
1527-8999
CONICET Digital
CONICET
url http://hdl.handle.net/11336/165532
identifier_str_mv Cristófalo, Alejandro Ezequiel; Cano, María Emilia; Uhrig, María Laura; Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives; John Wiley & Sons Inc.; Chemical Record; 21; 10; 6-2021; 2808-2836
1527-8999
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/tcr.202100146
info:eu-repo/semantics/altIdentifier/doi/10.1002/tcr.202100146
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons Inc.
publisher.none.fl_str_mv John Wiley & Sons Inc.
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1842269368551997440
score 13.13397

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