Study of CH/π Interactions in the Molecular Recognition between Acetyl Galactopyranoside and 6-substituted 2-Methoxypyridinesand 2(1H)-Pyridones
A series of 6-substituted 2-methoxypyridine and 2(1H)-pyr-idones was designed and synthesized for its evaluation in the molecu-lar recognition of acetyl 2,3,4,6-tetra-O-methyl-b-D-galactopyranosidesubstrate.1H-NMR titration (affinity constantKadetermination) andchemical shift perturbation experiment...
| Autores: | , , |
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| Tipo de documento: | artigo |
| Estado: | Versão publicada |
| Data de publicação: | 2017 |
| País: | México |
| Recursos: | Universidad Nacional Autónoma de México |
| Repositório: | Redalyc-UNAM |
| OAI Identifier: | oai:redalyc.org:47553303005 |
| Acesso em linha: | https://www.redalyc.org/articulo.oa?id=47553303005 |
| Access Level: | Acceso aberto |
| Palavra-chave: | Química CH non glycosides pinteractions covalent interactions |
| Resumo: | A series of 6-substituted 2-methoxypyridine and 2(1H)-pyr-idones was designed and synthesized for its evaluation in the molecu-lar recognition of acetyl 2,3,4,6-tetra-O-methyl-b-D-galactopyranosidesubstrate.1H-NMR titration (affinity constantKadetermination) andchemical shift perturbation experiments were performed to evaluatethe capacity of these receptors to form CH/pinteractions with the sub-strate. The addition of 2-methoxypyridines to the substrate effectedup-field shift for the H3, H4and H5proton signals and down-field shiftfor the H2proton signal of galactopyranoside substrate. The deter-mined affinity constantKavalues for the association between2(1H)-pyridones and galactopyranoside showed that molecular recog-nition was weak. These results have demonstrated the existence ofweak CH/pinteractions and have reflected their weak intermolecularnature. Finally DFT calculations were performed to illustrate the ge-ometry of the molecular recognition between 2(1H)-pyridones andgalactopyranoside. |
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