Synthesis of N-glycosyl amides: conformational analysis and evaluation as inhibitors of β-galactosidase from E. coli
2023 Impact factor: 3.9
| Main Authors: | , , , |
|---|---|
| Other Authors: | |
| Format: | info:eu-repo/semantics/publishedVersion |
| Language: | eng |
| Published: |
2024
|
| Subjects: | |
| Online Access: | 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 |
| _version_ | 1807371478105063424 |
|---|---|
| author | Traverssi, Miqueas G. Manzano, Verónica E. Varela, Oscar Colomer, Juan P. |
| 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. |
| author_sort | Traverssi, Miqueas G. |
| collection | Repositorio Digital Universitario |
| description | 2023 Impact factor: 3.9 |
| format | info:eu-repo/semantics/publishedVersion |
| id | rdu-unc.553155 |
| institution | Universidad Nacional de Cordoba |
| language | eng |
| publishDate | 2024 |
| record_format | dspace |
| spelling | rdu-unc.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/ |
| 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 |
| title | 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_short | 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 |
| topic | N-glycosyl amides Sequential synthesis N-glycosyl Glycosyl azides |
| 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 |
| work_keys_str_mv | AT traverssimiqueasg synthesisofnglycosylamidesconformationalanalysisandevaluationasinhibitorsofbgalactosidasefromecoli AT manzanoveronicae synthesisofnglycosylamidesconformationalanalysisandevaluationasinhibitorsofbgalactosidasefromecoli AT varelaoscar synthesisofnglycosylamidesconformationalanalysisandevaluationasinhibitorsofbgalactosidasefromecoli AT colomerjuanp synthesisofnglycosylamidesconformationalanalysisandevaluationasinhibitorsofbgalactosidasefromecoli |