Publication
Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones: evaluation of their antimicrobial activity and toxicity
| authorProfile.affiliation | Instituto Politécnico de Santarém, Escola Superior Agrária de Santarém | pt_PT |
| dc.contributor.author | Xavier, N. M. | |
| dc.contributor.author | Goulart, Margarida | |
| dc.contributor.author | Neves, Ana Maria | |
| dc.contributor.author | Justino, Jorge | |
| dc.contributor.author | Chambert, S. | |
| dc.contributor.author | Rauter, A. P. | |
| dc.contributor.author | Queneau, Y. | |
| dc.date.accessioned | 2011-05-31T14:01:39Z | |
| dc.date.available | 2011-05-31T14:01:39Z | |
| dc.date.issued | 2011-01-15 | |
| dc.description.abstract | The synthesis of a series of pyranoid derivatives comprising a conjugated carbonyl function and related triazole derivatives, structurally suitable for bioactivity evaluation, was achieved in few steps starting from readily available carboxymethyl glycoside lactones (CMGL). 3-Enopyranosid-2-uloses were generated by oxidation/elimination of tri-O-acylated 2-hydroxy pyranosides. Subsequent Wittig olefination provided stereoselectively 2-C-branched-chain conjugated dienepyranosides with (E)-configuration around the exocyclic double bond. A heterogeneous CuI/Amberlyst-catalyzed 'click' chemistry protocol was used to convert glycosides bearing a propargyl moiety into the corresponding 1,2,3-triazoles. These new molecules were screened for their in vitro antibacterial and antifungal activities and those containing conjugated carbonyl systems demonstrated the best efficacy. (N-Dodecylcarbamoyl)methyl enone glycerosides were the most active ones among the enones tested. The alpha-anomer displayed very strong activities against Bacillus cereus and Bacillus subtilis and strong activity toward Enterococcus faecalis and the fungal pathogen Penicillium aurantiogriseum. The corresponding beta-anomer presented a very strong inhibitory effect against two fungal species (Aspergillus niger and P. aurantiogriseum). (N-Dodecyl-/N-propargyl/or N-benzylcarbamoyl) methyl dienepyranosides exhibited selectively a strong activity toward E. faecalis. Further acute toxicity evaluation indicated low toxic effect of the (N-dodecylcarbamoyl)methyl enone glyceroside alpha-anomer and of the carbamoylmethyl dienepyranosides N-protected with propargyl or benzyl groups | por |
| dc.identifier.citation | XAVIER; N.M.;GOULART, M. ; NEVES, A.; JUSTINO, J. CHAMBERT, S. RAUTER, A.P. ; Queneau, Y. (2011) - Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones. Evaluation of their antimicrobial activity and toxicity. Bioorganic & medicinal chemistry 19 (2): 926-938 | por |
| dc.identifier.issn | 0968-0896 | |
| dc.identifier.uri | http://hdl.handle.net/10400.15/443 | |
| dc.language.iso | eng | por |
| dc.peerreviewed | yes | por |
| dc.publisher | Elsevier | por |
| dc.relation.publisherversion | http://www.elsevier.com/locate/bmc | por |
| dc.subject | Bicyclic sugar lactones | por |
| dc.subject | Sugar enones | por |
| dc.subject | Diene pyranosides | por |
| dc.subject | Antimicrobial activity | por |
| dc.title | Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones: evaluation of their antimicrobial activity and toxicity | por |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.citation.conferencePlace | Amesterdão | por |
| oaire.citation.endPage | 938 | por |
| oaire.citation.startPage | 926 | por |
| oaire.citation.title | Bioorganic & medicinal chemistry | por |
| person.familyName | Neves | |
| person.familyName | Justino | |
| person.givenName | Ana Maria | |
| person.givenName | Jorge | |
| person.identifier.ciencia-id | 751F-D764-23D4 | |
| person.identifier.orcid | 0000-0003-2130-7960 | |
| person.identifier.orcid | 0000-0003-3114-5926 | |
| rcaap.rights | openAccess | por |
| rcaap.type | article | por |
| relation.isAuthorOfPublication | 8881a916-c912-44ac-a75d-ad1703f77ebb | |
| relation.isAuthorOfPublication | 3e483773-36b8-4a7b-82f3-c0a39f6a7fa9 | |
| relation.isAuthorOfPublication.latestForDiscovery | 8881a916-c912-44ac-a75d-ad1703f77ebb |