Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/15141
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Campo DC | Valor | Idioma |
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dc.contributor.author | Alves, M. José | - |
dc.contributor.author | Costa, Flora Teixeira e | - |
dc.contributor.author | Duarte, Vera C. M. | - |
dc.contributor.author | Fortes, A. Gil | - |
dc.contributor.author | Martins, J. A. R. | - |
dc.contributor.author | Micaelo, N. M. | - |
dc.date.accessioned | 2011-12-13T15:58:11Z | - |
dc.date.available | 2011-12-13T15:58:11Z | - |
dc.date.issued | 2011 | - |
dc.identifier.issn | 0022-3263 | por |
dc.identifier.issn | 1520-6904 | por |
dc.identifier.uri | https://hdl.handle.net/1822/15141 | - |
dc.description.abstract | - A new expeditious preparation of homochiral (-)-1-azafagomine, and (+)-5-epi-1-azafagomine has been devised. Stoodley´s diastereoselective cycloaddition of dienes bearing a 2,3,4,6-tetraacetyl glucosyl chiral auxiliary to 4-phenyl-1,2,4-triazole-3,5-dione, was merged with Bols protocol for functionalizing alkenes into molecules bearing a glucosyl framework. Homochiral (+)-5-epi-1-azafagomine was synthetized for the first time. Partial reductive cleavage of the phenyltriazolidinone moiety afforded new homochiral 1-N-phenyl carboxamide derivatives of 1-azafagomine. Both enantiomers of these derivatives were synthetized and tested, displaying a very good enzymatic inhibition towards baker´s yeast α-glucosidase. The molecular recognition mechanism of the 1-N-phenyl carboxamide derivative of 1-azafagomine by α-glucosidase from baker´s yeast was studied by molecular modelling. The efficient packing of the aromatic ring of the 1-N-phenyl carboxamide moiety into a hydrophobic sub-site (pocket) in the enzyme´s active site, seems to be responsible for the improved binding affinity in relation to underivatized (-)1-azafagomine and (+)1-azafagomine. | por |
dc.description.sponsorship | We thank FCT for project funding PTDC/QUI/67407/2006 and FCT and FEDER for funding NMR spectrometer Bruker Avance III 400 as part of the National NMR Network. M.N.M. acknowledges the contract research program "Compromisso com a Ciencia" Reference C2008-UMINHO-CQ-03 and access to the Minho University GRIUM cluster. | por |
dc.language.iso | eng | por |
dc.publisher | American Chemical Society (ACS) | por |
dc.relation | info:eu-repo/grantAgreement/FCT/5876-PPCDTI/67407/PT | - |
dc.rights | openAccess | por |
dc.subject | Diels-Alder | por |
dc.subject | Iminosugars | por |
dc.subject | 1-azafagomine derivatives | por |
dc.subject | Glycosidase inhibitors | por |
dc.subject | Synthesis | por |
dc.title | Advances in the synthesis of Homochiral (-)-1-azafagomine and (+)-5-epi-1-azafagomine. 1-N-phenyl carboxamide derivatives of both enantiomers of 1-azafagomine: leads for the synthesis of active α-Glycosidase inhibitors | por |
dc.type | article | por |
dc.peerreviewed | yes | por |
dc.relation.publisherversion | http://pubs.acs.org/ | por |
sdum.publicationstatus | published | por |
oaire.citationStartPage | 9584 | por |
oaire.citationEndPage | 9592 | por |
oaire.citationIssue | 23 | por |
oaire.citationTitle | The Journal of Organic Chemistry | por |
oaire.citationVolume | 76 | por |
dc.identifier.doi | 10.1021/jo201486q | - |
dc.identifier.pmid | 22017265 | por |
dc.subject.wos | Science & Technology | por |
sdum.journal | The Journal of Organic Chemistry | por |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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Vera-JOC-2011.pdf | manuscript | 1,36 MB | Adobe PDF | Ver/Abrir |