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Synthesis and Biological Activity of 3,4,-Tri-О-Acetyl-N-Acetylglucosamine and Tetraacetylglucopyranose Conjugated with Alkyl Phosphates

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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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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 420088, Kazan, Russia

    R. R. Sharipova, B. F. Garifullin, A. S. Sapunova, A. D. Voloshina & V. E. Kataev

  2. Ural Research Institute for Phthisiopulmonology, 620039, Yekaterinburg, Russia

    M. A. Kravchenko

Authors
  1. R. R. Sharipova
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  2. B. F. Garifullin
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  3. A. S. Sapunova
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  4. A. D. Voloshina
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  5. M. A. Kravchenko
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  6. V. E. Kataev
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Corresponding author

Correspondence to V. E. Kataev.

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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.

Corresponding author: phone: +7 (843) 273-9365; fax: +7 (843) 273-2253; e-mail: kataev@iopc.ru.

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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

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