BIBLIOS

Document type
Journal articles

Document subtype
Full paper

Title
Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against Bacillus anthracis

Participants in the publication
Catarina Dias (Author)
Alice Martins (Author)
Ana Pelerito (Author)
Maria C. Oliveira (Author)
Marialessandra Contino (Author)
Nicola A. Colabufo (Author)
Amélia P. Rauter (Author)
Dep. Química e Bioquímica
CQB

Summary
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-arabinopyranoside 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-α-D-xylo-hexopyranoside remains a promising glycoside, presenting low MIC values for all species tested, and low cytotoxicity in intestinal and liver cell models.


Institution
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Where published
European Journal of Organic Chemistry

Publication Identifiers
ISSN - 1434-193X

Publisher
Wiley



Document Identifiers
DOI - https://doi.org/10.1002/ejoc.201801764
URL - http://dx.doi.org/10.1002/ejoc.201801764

Rankings
SCIMAGO Q1 (2018) - 0.987 - Organic Chemistry
Web Of Science Q1 (2018) - 3.029 - Organic Chemistry

Keywords
Anthrax Deoxygenation Glycosides Antimicrobial

Notes
I am the corresponding author

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