BIBLIOS

Tipo
Artigos em Revista

Tipo de Documento
Artigo Completo

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

Participantes na publicação
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

Resumo
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.


Instituição
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Suporte
European Journal of Organic Chemistry

Identificadores da Publicação
ISSN - 1434-193X

Editora
Wiley



Identificadores do Documento
DOI - https://doi.org/10.1002/ejoc.201801764
URL - http://dx.doi.org/10.1002/ejoc.201801764

Identificadores de Qualidade
SCIMAGO Q1 (2018) - 0.987 - Organic Chemistry
Web Of Science Q1 (2018) - 3.029 - Organic Chemistry

Keywords
Anthrax Deoxygenation Glycosides Antimicrobial

Anotações
I am the corresponding author

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