Publication Type Journal Article
Title Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against Bacillus anthracis
Authors Catarina Dias Alice Martins Ana Pelerito Maria C. Oliveira Marialessandra Contino Nicola A. Colabufo Amélia P. Rauter
Groups HC
Journal EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Year 2019
Month March
Volume
Number 12
Pages 2224-2233
Abstract The discovery of the bactericide dodecyl 2,6-dideoxypyranoside reorganizing membrane phospholipid matrix of Bacillus species into a hexagonal phase, encouraged further research on glycone deoxygenation/bioactivity relationship. We now describe expedient syntheses of new 2-, 3-, 4-deoxy, 2,3- and 3,4-dideoxy glycosides in moderate to good yields. Interestingly, Amberlyst 15 is a key protagonist, efficiently applied for the transacetalation of alkyl deoxy glycosides and for ring contraction to access regioselectively hexofuranosides. The 2-deoxy-d-arabino pyranoside affords the higher MIC values against two Bacillus spp. and Enterococcus faecalis, while a 4-fold decrease or higher was found by inversion of configuration or by deoxygenation at C-3. While 2,3- and 3,4-dideoxygenation do not improve bioactivity, the 4,6-dideoxy-alpha-d-xylo-hexopyranoside remains a promising glycoside, presenting low MIC values for all species tested, and low cytotoxicity in intestinal and liver cell models.
DOI http://dx.doi.org/10.1002/ejoc.201801764
ISBN
Publisher
Book Title
ISSN 1434-193X
EISSN 1099-0690
Conference Name
Bibtex ID ISI:000462777400004
Observations
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