Synthesis and antimicrobial activity of 6-sulfo-6-deoxy-D-glucosamine and its derivatives - Publication - MOST Wiedzy

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Synthesis and antimicrobial activity of 6-sulfo-6-deoxy-D-glucosamine and its derivatives

Abstract

6-Sulfo-6-deoxy-D-glucosamine (GlcN6S), 6-sulfo-6-deoxy-D-glucosaminitol (ADGS) and their N-acetyl and methyl ester derivatives have been synthesized and tested as inhibitors of enzymes catalyzing reactions of the UDP-GlcNAc pathway in bacteria and yeasts. GlcN6S and ADGS at micromolar concentrations inhibited glucosamine-6-phosphate (GlcN6P) synthase of microbial origin. The former was also inhibitory towards fungal GlcN6P N-acetyl transferase, but at millimolar concentrations. Both compounds and their N-acetyl derivatives exhibited antimicrobial in vitro activity, with MICs in the 0.125–2.0 mg mL−1 range. Antibacterial but not antifungal activity of GlcN6S was potentiated by D-glucosamine and a synergistic antibacterial effect was observed for combination of ADGP and a dipeptide Nva-FMDP.

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Details

Category:
Magazine publication
Type:
artykuł w czasopiśmie wyróżnionym w JCR
Published in:
CARBOHYDRATE RESEARCH no. 448, pages 79 - 87,
ISSN: 0008-6215
Language:
English
Publication year:
2017
Bibliographic description:
Skarbek K., Gabriel I., Szweda P., Wojciechowski M., Khan M., Boris G., Milewski S., Milewska M.: Synthesis and antimicrobial activity of 6-sulfo-6-deoxy-D-glucosamine and its derivatives// CARBOHYDRATE RESEARCH. -Vol. 448, (2017), s.79-87
DOI:
Digital Object Identifier (open in new tab) 10.1016/j.carres.2017.06.002
Verification:
Gdańsk University of Technology

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