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

Show simple item record Rauter, AP en Lucas, S en Almeida, T en Sacoto, D en Ribeiro, V en Justino, J en Neves, A en Oliveira, Maria en Oliveira, MC en Ferreira, MJ en Santos, MS en Barbosa, E en 2014-02-16T21:53:31Z en 2005-02-07 en
dc.identifier.citation Carbohydrate Research 340(2):191-201 07 Feb 2005 en
dc.identifier.issn 0008-6215 en
dc.identifier.uri en
dc.description.abstract Synthesis 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. en
dc.language English en
dc.publisher ELSEVIER SCI LTD en
dc.relation.ispartofseries Carbohydrate Research en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from en
dc.rights.uri en
dc.subject Science & Technology en
dc.subject Life Sciences & Biomedicine en
dc.subject Physical Sciences en
dc.subject Biochemistry & Molecular Biology en
dc.subject Chemistry, Applied en
dc.subject Chemistry, Organic en
dc.subject Chemistry en
dc.subject CHEMISTRY, APPLIED en
dc.subject CHEMISTRY, ORGANIC en
dc.subject alkyl 2,6-dideoxy-L-arabino-hexopyranosides en
dc.subject synthesis en
dc.subject interfacial properties en
dc.subject non-ionic sugar surfactants en
dc.subject antimicrobial activity en
dc.subject GLYCALS en
dc.subject AGGREGATION en
dc.subject GLYCOSIDATIONS en
dc.subject ADSORPTION en
dc.subject HEADGROUP en
dc.subject ESTERS en
dc.subject WATER en
dc.title Synthesis, surface active and antimicrobial properties of new alkyl 2,6-dideoxy-L-arabino-hexopyranosides en
dc.type Journal Article en
dc.identifier.doi 10.1016/j.carres.2004.11.020 en
pubs.issue 2 en
pubs.begin-page 191 en
pubs.volume 340 en
dc.identifier.pmid 15639239 en en
pubs.end-page 201 en
pubs.publication-status Published en
dc.rights.accessrights en
pubs.subtype Article en
pubs.elements-id 163197 en
dc.identifier.eissn 1873-426X en
pubs.record-created-at-source-date 2014-02-17 en
pubs.dimensions-id 15639239 en

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