Abstract
Conjugates of 3,4,6-tri-О-acetyl-N-acetylglucosamine and tetraacetyl glucopyranose with alkyl phosphates were synthesized. The dependence of their antibacterial and antituberculosis activities on the length of the alkyl substituent at the phosphate group was found. The conjugates with a decyl substituent exhibited in vitro the highest antituberculosis activity against Mycobacterium tuberculosis H37Rv (MIC 3 µg/mL) but the weakest effect towards Streptococcus aureus and Bacillus cereus (≤MIC 125 µg/mL). Vice versa, the conjugates with a cetyl substituent demonstrated the highest antibacterial activity in vitro towards S. aureus and B. cereus (MIC 16 µg/mL) but showed the lowest antituberculosis activity (MIC 12 µg/mL) among the compounds under study.
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ACKNOWLEDGMENTS
The study of antituberculosis activity of the compounds was supported by the Russian Science Foundation, project no. 14-50-00014. The authors gratefully acknowledge the Assigned Spectral–Analytical Center of FRC Kazan Scientific Center of RAS.
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The authors declare that they have no conflict of interest. This article does not contain any studies involving animals or human participants performed by any of the authors.
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Translated by E. Shirokova
Abbreviations: GlcNAc, N-acetylglucosamine; GlmU-T, Gl-cNAc-1P-uridyl transferase; PG-T, PG glycosyl transferase; GlcNAc-1-P-alkyl, N-acetylglucosamine 1-alkylphosphate; MIC, minimal inhibitory concentration; PG, peptidoglycan; TMS-OTF, trimethylsilyl trifluoromethanesulfonate.
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Sharipova, R.R., Garifullin, B.F., Sapunova, A.S. et al. Synthesis and Biological Activity of 3,4,-Tri-О-Acetyl-N-Acetylglucosamine and Tetraacetylglucopyranose Conjugated with Alkyl Phosphates. Russ J Bioorg Chem 45, 155–164 (2019). https://doi.org/10.1134/S1068162019020110
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DOI: https://doi.org/10.1134/S1068162019020110