Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli

Autores
Traverssi, Miqueas Gabriel; Manzano, Veronica Elena; Varela, Oscar Jose; Colomer, Juan Pablo
Año de publicación
2024
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis of N-glycosyl amides typically involves the use of glycosyl amines as direct precursors, resulting in low yields due to hydrolysis and the loss of stereocontrol through anomerization processes. In this study, a sequential synthesis of N-glycosyl amides is proposed, employing glycosyl amines as intermediates obtained from glycosyl azides. Derivatives with gluco, galacto, or xylo configurations were synthesized. Hexose derivatives were obtained under stereocontrol to give only the β anomer, while the xylo derivatives provided a mixture of α and β anomers. Conformational analysis revealed that all β anomers adopted the 4C1 conformation, while α anomers were found in the 1C4 chair as the major conformer. After de-O-acetylation, the derivatives containing a galactose unit were evaluated as inhibitors of β-galactosidase from E. coli and were found to be moderate inhibitors.
Fil: Traverssi, Miqueas Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Manzano, Veronica Elena. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Colomer, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Materia
CARBOHYDRATES
N-GLYCOSYLAMIDES
CONFORMATIONAL ANALYSIS
ENZYMATIC INHIBITION
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/259107
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/259107
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coliTraverssi, Miqueas GabrielManzano, Veronica ElenaVarela, Oscar JoseColomer, Juan PabloCARBOHYDRATESN-GLYCOSYLAMIDESCONFORMATIONAL ANALYSISENZYMATIC INHIBITIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis of N-glycosyl amides typically involves the use of glycosyl amines as direct precursors, resulting in low yields due to hydrolysis and the loss of stereocontrol through anomerization processes. In this study, a sequential synthesis of N-glycosyl amides is proposed, employing glycosyl amines as intermediates obtained from glycosyl azides. Derivatives with gluco, galacto, or xylo configurations were synthesized. Hexose derivatives were obtained under stereocontrol to give only the β anomer, while the xylo derivatives provided a mixture of α and β anomers. Conformational analysis revealed that all β anomers adopted the 4C1 conformation, while α anomers were found in the 1C4 chair as the major conformer. After de-O-acetylation, the derivatives containing a galactose unit were evaluated as inhibitors of β-galactosidase from E. coli and were found to be moderate inhibitors.Fil: Traverssi, Miqueas Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Manzano, Veronica Elena. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Colomer, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaRoyal Society of Chemistry2024-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/259107Traverssi, Miqueas Gabriel; Manzano, Veronica Elena; Varela, Oscar Jose; Colomer, Juan Pablo; Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli; Royal Society of Chemistry; RSC Advances; 14; 4; 1-2024; 2659-26722046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/d3ra07763binfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:59:28Zoai:ri.conicet.gov.ar:11336/259107instacron: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:34982025-09-29 09:59:29.2CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli
title Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli
spellingShingle Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli
Traverssi, Miqueas Gabriel
CARBOHYDRATES
N-GLYCOSYLAMIDES
CONFORMATIONAL ANALYSIS
ENZYMATIC INHIBITION
title_short Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli
title_full Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli
title_fullStr Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli
title_full_unstemmed Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli
title_sort Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli
dc.creator.none.fl_str_mv Traverssi, Miqueas Gabriel
Manzano, Veronica Elena
Varela, Oscar Jose
Colomer, Juan Pablo
author Traverssi, Miqueas Gabriel
author_facet Traverssi, Miqueas Gabriel
Manzano, Veronica Elena
Varela, Oscar Jose
Colomer, Juan Pablo
author_role author
author2 Manzano, Veronica Elena
Varela, Oscar Jose
Colomer, Juan Pablo
author2_role author
author
author
dc.subject.none.fl_str_mv CARBOHYDRATES
N-GLYCOSYLAMIDES
CONFORMATIONAL ANALYSIS
ENZYMATIC INHIBITION
topic CARBOHYDRATES
N-GLYCOSYLAMIDES
CONFORMATIONAL ANALYSIS
ENZYMATIC INHIBITION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The synthesis of N-glycosyl amides typically involves the use of glycosyl amines as direct precursors, resulting in low yields due to hydrolysis and the loss of stereocontrol through anomerization processes. In this study, a sequential synthesis of N-glycosyl amides is proposed, employing glycosyl amines as intermediates obtained from glycosyl azides. Derivatives with gluco, galacto, or xylo configurations were synthesized. Hexose derivatives were obtained under stereocontrol to give only the β anomer, while the xylo derivatives provided a mixture of α and β anomers. Conformational analysis revealed that all β anomers adopted the 4C1 conformation, while α anomers were found in the 1C4 chair as the major conformer. After de-O-acetylation, the derivatives containing a galactose unit were evaluated as inhibitors of β-galactosidase from E. coli and were found to be moderate inhibitors.
Fil: Traverssi, Miqueas Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Manzano, Veronica Elena. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Colomer, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
description The synthesis of N-glycosyl amides typically involves the use of glycosyl amines as direct precursors, resulting in low yields due to hydrolysis and the loss of stereocontrol through anomerization processes. In this study, a sequential synthesis of N-glycosyl amides is proposed, employing glycosyl amines as intermediates obtained from glycosyl azides. Derivatives with gluco, galacto, or xylo configurations were synthesized. Hexose derivatives were obtained under stereocontrol to give only the β anomer, while the xylo derivatives provided a mixture of α and β anomers. Conformational analysis revealed that all β anomers adopted the 4C1 conformation, while α anomers were found in the 1C4 chair as the major conformer. After de-O-acetylation, the derivatives containing a galactose unit were evaluated as inhibitors of β-galactosidase from E. coli and were found to be moderate inhibitors.
publishDate 2024
dc.date.none.fl_str_mv 2024-01
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/11336/259107
Traverssi, Miqueas Gabriel; Manzano, Veronica Elena; Varela, Oscar Jose; Colomer, Juan Pablo; Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli; Royal Society of Chemistry; RSC Advances; 14; 4; 1-2024; 2659-2672
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/259107
identifier_str_mv Traverssi, Miqueas Gabriel; Manzano, Veronica Elena; Varela, Oscar Jose; Colomer, Juan Pablo; Synthesis of N -glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli; Royal Society of Chemistry; RSC Advances; 14; 4; 1-2024; 2659-2672
2046-2069
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/d3ra07763b
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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_ 1844613764568055808
score 13.070432

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