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Synthesis, surface active and antimicrobial properties of new alkyl 2,6-dideoxy-L-arabino-hexopyranosides

2005-02Journal article Open access
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dc.contributor.authorRauter, A. P.
dc.contributor.authorLucas, S.
dc.contributor.authorAlmeida, T.
dc.contributor.authorSacoto, D.
dc.contributor.authorRibeiro, V.
dc.contributor.authorJustino, Jorge
dc.contributor.authorNeves, Ana
dc.contributor.authorV.M. Silva, Filipa
dc.contributor.authorOliveira, M.C.
dc.contributor.authorFerreira, M.J.
dc.contributor.authorSantos, M.S.
dc.contributor.authorBarbosa, E.
dc.date.accessioned2023-09-12T18:02:45Z
dc.date.available2023-09-12T18:02:45Z
dc.date.issued2005-02
dc.description.abstractSynthesis of alkyl 2,6-dideoxy-L-arabino-hexopyranosides was accomplished by the reaction of 1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol with fatty alcohols in dichloromethane, catalyzed by triphenylphosphine hydrobromide. Reaction with octanol and dodecanol gave the corresponding α-glycosides in 50% and 42% yield, the β-glycosides in 20% and 21% yield and the α-anomer of the Ferrier product in 10% and 9% yield, respectively.Deacetylation of the α-/β-glycosides with sodium methoxide in methanol afforded the amphiphilic L-arabino-hexopyranosides in 94–99% yield. The surface tension at the air–water interface of the octyl L-glycosides and of the dodecyl α-L-glycoside aqueous solutions at 35 °C was measured with a du Noüy ring tensiometer and surface properties such as critical micelle concentration (CMC), relative surface excess, molecular area at the interface and Gibbs micellization free energy were evaluated. The stereochemistry of the hexopyranoside ring in unimers and aggregates is correlated to the hydrophobicity and packing efficiency on the air–water interface. The antibacterial and antifungal activities of the surface-active glycosides were evaluated using the paper disk diffusion method. The dodecyl α-L-arabino-hexopyranoside was quite active over Bacillus cereus and Bacillus subtilis, while low activity was found for this glycoside over Enterococcus faecalis and Listeria monocytogenes. The octyl glycosides tested showed low activity over almost all the above-mentioned bacteria, and also over the fungus Candida albicans. No inhibition of Salmonella enteritidis and of the filamentous fungus Aspergillus niger was detected for any of the compounds tested.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationRauter A.P.; Lucas, S.; Almeida, T.; Sacoto, D.; Ribeiro, V.; Justino, J.; Neves, A; Silva, F.V.M.; Oliveira, M.C.; Ferreira, M.J.; Santos, M.S. & Barbosa, E. (2005). Synthesis, surface active and antimicrobial properties of new alkyl 2,6-dideoxy-L-arabino-hexopyranosides. Carbohydrate Research, 340(2), 191-201. DOI:10.1016/j.carres.2004.11.020pt_PT
dc.identifier.doidoi.org/10.1016/j.carres.2004.11.020pt_PT
dc.identifier.issn0008-6215
dc.identifier.urihttp://hdl.handle.net/10400.15/4534
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.relation.publisherversionhttps://www.sciencedirect.com/science/article/pii/S0008621504004999?via%3Dihubpt_PT
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjectalkyl 2,6-dideoxy-L-arabino-hexopyranosidespt_PT
dc.subjectsynthesispt_PT
dc.subjectinterfacial propertiespt_PT
dc.subjectnon-ionic sugar surfactantspt_PT
dc.subjectantimicrobial activitypt_PT
dc.titleSynthesis, surface active and antimicrobial properties of new alkyl 2,6-dideoxy-L-arabino-hexopyranosidespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage201pt_PT
oaire.citation.issue2pt_PT
oaire.citation.startPage191pt_PT
oaire.citation.titleCarbohydrate Researchpt_PT
oaire.citation.volume340pt_PT
person.familyNameJustino
person.familyNameNeves
person.familyNameVinagre Marques da Silva
person.givenNameJorge
person.givenNameAna Maria
person.givenNameFilipa
person.identifierhttps://scholar.google.pt/citations?hl=pt-PT&user=TcUz9ZAAAAAJ
person.identifier.ciencia-id751F-D764-23D4
person.identifier.ciencia-idB610-66DA-A3AC
person.identifier.orcid0000-0003-3114-5926
person.identifier.orcid0000-0003-2130-7960
person.identifier.orcid0000-0003-4700-2938
person.identifier.scopus-author-id22942414000
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication3e483773-36b8-4a7b-82f3-c0a39f6a7fa9
relation.isAuthorOfPublication8881a916-c912-44ac-a75d-ad1703f77ebb
relation.isAuthorOfPublication344bf736-31c9-4a35-844c-67a176174a44
relation.isAuthorOfPublication.latestForDiscovery8881a916-c912-44ac-a75d-ad1703f77ebb

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