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

2023 Impact factor: 3.9

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Detalles Bibliográficos
Autores principales: Traverssi, Miqueas G., Manzano, Verónica E., Varela, Oscar, Colomer, Juan P.
Otros Autores: https://orcid.org/0000-0002-3763-3181
Formato: publishedVersion article
Lenguaje:Inglés
Publicado: 2024
Materias:
N-glycosyl amides
Sequential synthesis
N-glycosyl
Glycosyl azides
Acceso en línea:http://hdl.handle.net/11086/553155
https://pubs.rsc.org/en/content/articlehtml/2024/ra/d3ra07763b
https://pubmed.ncbi.nlm.nih.gov/38229710/
https://doi.org/10.1039/d3ra07763b
Aporte de:
Repositorio Digital Universitario (UNC) de Universidad Nacional de Córdoba
id I10-R141-11086-553155
record_format dspace
institution Universidad Nacional de Córdoba
institution_str I-10
repository_str R-141
collection Repositorio Digital Universitario (UNC)
language Inglés
topic N-glycosyl amides
Sequential synthesis
N-glycosyl
Glycosyl azides
spellingShingle N-glycosyl amides
Sequential synthesis
N-glycosyl
Glycosyl azides
Traverssi, Miqueas G.
Manzano, Verónica E.
Varela, Oscar
Colomer, Juan P.
Synthesis of N-glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli
topic_facet N-glycosyl amides
Sequential synthesis
N-glycosyl
Glycosyl azides
description 2023 Impact factor: 3.9
author2 https://orcid.org/0000-0002-3763-3181
author_facet https://orcid.org/0000-0002-3763-3181
Traverssi, Miqueas G.
Manzano, Verónica E.
Varela, Oscar
Colomer, Juan P.
format publishedVersion
article
author Traverssi, Miqueas G.
Manzano, Verónica E.
Varela, Oscar
Colomer, Juan P.
author_sort Traverssi, Miqueas G.
title Synthesis of N-glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli
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
publishDate 2024
url http://hdl.handle.net/11086/553155
https://pubs.rsc.org/en/content/articlehtml/2024/ra/d3ra07763b
https://pubmed.ncbi.nlm.nih.gov/38229710/
https://doi.org/10.1039/d3ra07763b
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AT varelaoscar synthesisofnglycosylamidesconformationalanalysisandevaluationasinhibitorsofbgalactosidasefromecoli
AT colomerjuanp synthesisofnglycosylamidesconformationalanalysisandevaluationasinhibitorsofbgalactosidasefromecoli
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spelling I10-R141-11086-5531552024-08-07T06:21:53Z Synthesis of N-glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli Traverssi, Miqueas G. Manzano, Verónica E. Varela, Oscar Colomer, Juan P. https://orcid.org/0000-0002-3763-3181 https://orcid.org/0000-0002-0952-608X https://orcid.org/0000-0002-5527-7088 N-glycosyl amides Sequential synthesis N-glycosyl Glycosyl azides 2023 Impact factor: 3.9 info:eu-repo/semantics/publishedVersion Fil: Traverssi, Miqueas G. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Fil: Traverssi, Miqueas G. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Fisico-Química de Córdoba; Argentina. Fil: Manzano, Verónica E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Fil: Manzano, Verónica E. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro de Investigación en Hidratos de Carbono; Argentina. Fil: Varela, Oscar. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Fil: Varela, Oscar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro de Investigación en Hidratos de Carbono; Argentina. Fil: Colomer, Juan P. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Fil: Colomer, Juan P. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Fisico-Química de Córdoba; Argentina. 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. info:eu-repo/semantics/publishedVersion Fil: Traverssi, Miqueas G. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Fil: Traverssi, Miqueas G. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Fisico-Química de Córdoba; Argentina. Fil: Manzano, Verónica E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Fil: Manzano, Verónica E. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro de Investigación en Hidratos de Carbono; Argentina. Fil: Varela, Oscar. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Fil: Varela, Oscar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro de Investigación en Hidratos de Carbono; Argentina. Fil: Colomer, Juan P. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina. Fil: Colomer, Juan P. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Fisico-Química de Córdoba; Argentina. 2024-08-06T23:07:25Z 2024-08-06T23:07:25Z 2024-01-08 article Traverssi, M. G., Manzano, V. E., Varela, O., & Colomer, J. P. (2024). Synthesis of N-glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli. RSC advances, 14(4), 2659-2672. http://hdl.handle.net/11086/553155 2046-2069 https://pubs.rsc.org/en/content/articlehtml/2024/ra/d3ra07763b https://pubmed.ncbi.nlm.nih.gov/38229710/ https://doi.org/10.1039/d3ra07763b eng Attribution-NonCommercial 4.0 International http://creativecommons.org/licenses/by-nc/4.0/

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