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Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against Bacillus anthracis
Author(s) -
Dias Catarina,
Martins Alice,
Pelerito Ana,
Oliveira Maria C.,
Contino Marialessandra,
Colabufo Nicola A.,
Rauter Amélia P.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801764
Subject(s) - deoxygenation , chemistry , glycoside , enterococcus faecalis , antimicrobial , alkyl , phospholipid , stereochemistry , biochemistry , organic chemistry , membrane , catalysis , escherichia coli , gene
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‐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.