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‐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.
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