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

Authors :: Skarbek K
Gabriel I
Szweda P
Wojciechowski M
Khan MA
Görke B
Milewski S
Milewska MJ
Source :: Carbohydrate research [Carbohydr Res] 2017 Aug 07; Vol. 448, pp. 79-87. Date of Electronic Publication: 2017 Jun 12.
Publication Year :: 2017
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 <superscript>-1</superscript> 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.<br /> (Copyright © 2017 Elsevier Ltd. All rights reserved.)

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