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Publication details

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 - Centro de Química e Bioquímica 

Scope
International

Refereeing
Yes

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.

Date of Publication
2019-02-11

Institution
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Where published
European Journal of Organic Chemistry

Publication Identifiers
ISSN - 1434-193X

Publisher
Wiley

Volume
2019
Number
12

Number of pages
9
Starting page
2224
Last page
2233

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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APA
Catarina Dias, Alice Martins, Ana Pelerito, Maria C. Oliveira, Marialessandra Contino, Nicola A. Colabufo, Amélia P. Rauter, (2019). Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against Bacillus anthracis. European Journal of Organic Chemistry, 2019, 2224-2233. ISSN 1434-193X. eISSN . http://dx.doi.org/10.1002/ejoc.201801764

IEEE
Catarina Dias, Alice Martins, Ana Pelerito, Maria C. Oliveira, Marialessandra Contino, Nicola A. Colabufo, Amélia P. Rauter, "Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against Bacillus anthracis" in European Journal of Organic Chemistry, vol. 2019, pp. 2224-2233, 2019. 10.1002/ejoc.201801764

BIBTEX
@article{39346, author = {Catarina Dias and Alice Martins and Ana Pelerito and Maria C. Oliveira and Marialessandra Contino and Nicola A. Colabufo and Amélia P. Rauter}, title = {Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against Bacillus anthracis}, journal = {European Journal of Organic Chemistry}, year = 2019, pages = {2224-2233}, volume = 2019 }