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Their surface\u2010active properties were evaluated in terms of adsorption and aggregation parameters and compared with those of 2\u2010deoxy\u2010<jats:sc>D<\/jats:sc>\u2010glycosides and 2,6\u2010dideoxy\u2010<jats:sc>L<\/jats:sc>\u2010glycosides. Deoxygenation at the 6\u2010position led to a decrease in the critical micelle concentration, and an increase in the adsorption efficiency (pC<jats:sub>20<\/jats:sub>) promoting aggregation more efficiently than adsorption. With regard to the antibacterial activity, dodecyl 2,6\u2010dideoxy\u2010\u03b1\u2010<jats:sc>L<\/jats:sc>\u2010<jats:italic>arabino<\/jats:italic>\u2010hexopyranoside was the most active compound towards <jats:italic>Bacillus anthracis<\/jats:italic> (MIC 25 \u03bc<jats:sc>M<\/jats:sc>), whereas its enantiomer exhibited a MIC value of 50 \u03bc<jats:sc>M<\/jats:sc>. Both 2,6\u2010dideoxy glycosides were active towards <jats:italic>Bacillus cereus<\/jats:italic>, <jats:italic>Bacillus subtilis<\/jats:italic>, <jats:italic>Enterococcus faecalis<\/jats:italic> and <jats:italic>Listeria monocytogenes<\/jats:italic>. In contrast, none of the 2\u2010deoxy glycosides was significantly active. These results and the data on surface activity suggest that aggregation is a key issue for antimicrobial activity. Beyond infection, Alzheimer's disease also threatens elderly populations. In the search for butyrylcholinesterase (BChE) selective inhibition, 2\u2010deoxy glycosides were screened in vitro by using Ellman's assay. Octyl 2\u2010deoxy\u2010\u03b1\u2010<jats:sc>D<\/jats:sc>\u2010glycoside was found to be a BChE selective inhibitor promoting competitive inhibition. Docking studies supported these results as they pinpoint the importance of the primary OH group in stabilizing the BChE inhibitor complex. A size\u2010exclusion mechanism for inhibition has been proposed based on the fact that acetylcholinesterase (AChE) exhibits several bulky residues that hinder access to the active\u2010site cavity. This work shows how the deoxygenation pattern, configuration and functionality of the anomeric centre can tune physical and surface properties as well as the bioactivity of these multifunctional and stereochemically rich molecules.<\/jats:p>","DOI":"10.1002\/ejoc.201201520","type":"journal-article","created":{"date-parts":[[2013,2,18]],"date-time":"2013-02-18T18:54:40Z","timestamp":1361213680000},"page":"1448-1459","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Tuning the Bioactivity of Tensioactive Deoxy Glycosides to Structure: Antibacterial Activity Versus Selective Cholinesterase Inhibition Rationalized by Molecular Docking"],"prefix":"10.1002","volume":"2013","author":[{"given":"Alice","family":"Martins","sequence":"first","affiliation":[]},{"given":"Maria S.","family":"Santos","sequence":"additional","affiliation":[]},{"given":"Catarina","family":"Dias","sequence":"additional","affiliation":[]},{"given":"Patr\u00edcia","family":"Serra","sequence":"additional","affiliation":[]},{"given":"Vasco","family":"Cachatra","sequence":"additional","affiliation":[]},{"given":"Jo\u00e3o","family":"Pais","sequence":"additional","affiliation":[]},{"given":"Jo\u00e3o","family":"Caio","sequence":"additional","affiliation":[]},{"given":"V\u00edtor H.","family":"Teixeira","sequence":"additional","affiliation":[]},{"given":"Miguel","family":"Machuqueiro","sequence":"additional","affiliation":[]},{"given":"Marta S.","family":"Silva","sequence":"additional","affiliation":[]},{"given":"Ana","family":"Pelerito","sequence":"additional","affiliation":[]},{"given":"Jorge","family":"Justino","sequence":"additional","affiliation":[]},{"given":"Margarida","family":"Goulart","sequence":"additional","affiliation":[]},{"given":"Filipa V.","family":"Silva","sequence":"additional","affiliation":[]},{"given":"Am\u00e9lia P.","family":"Rauter","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2013,2,18]]},"reference":[{"key":"e_1_2_6_1_2","first-page":"3","volume":"305","author":"Rico\u2010Lattes I.","year":"2007","journal-title":"Actual. 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