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Synthesis of 1,2,3-triazole-linked glycohybrids in the gluco-, gulo-, and allopyranose series

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Chemistry of Heterocyclic Compounds Aims and scope

Ketone derived from diacetone-α-D-glucose is a suitable starting material for the synthesis of 3-C-linked glycohybrids containing 1,2,3-triazole moiety as an intersugar linkage. The pyranose tautomers of 3-deoxy-3-(1,2,3-1H-triazol-1-yl)glucose, 3-C-[(1,2,3-1Htriazol-1-yl)methyl]allose and 3-C-[(1,2,3-1H-triazol-1-yl)methyl]gulose moieties are released upon the acidic hydrolysis of the corresponding O-isopropylidene-protected furanosyl-type synthetic intermediates. Some of the title compounds show a rare property of activating β-galactosidase from Escherichia coli.

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This work was supported by the Latvian Council of Science (grant No. 10.0030). The authors thank JSC ''Olainfarm'' for kind donation of diacetone-D-glucose. JSC ''Grindeks'' is acknowledged for kind donation of organic solvents. The authors are indebted to Syntagon Baltic and Professor E. Liepinsh for the help with NMR analysis of some compounds. J. Uzuleņa thanks JSC ''Olainfarm'' and the Latvian Academy of Sciences for scholarships.

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Authors and Affiliations

  1. Institute of Technology of Organic Chemistry, Riga Technical University, 3/7 P. Valdena St., Riga, LV-1048, Latvia

    Jevgeņija Uzuleņa, Vitālijs Rjabovs & Māris Turks

  2. Department of Organic Chemistry, Faculty of Chemistry, University of Seville, 1 C/Prof. García González, Seville, E-41002, Spain

    Antonio J. Moreno-Vargas

Authors
  1. Jevgeņija Uzuleņa
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  2. Vitālijs Rjabovs
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  3. Antonio J. Moreno-Vargas
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  4. Māris Turks
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Correspondence to Māris Turks.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(7), 664–671

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Uzuleņa, J., Rjabovs, V., Moreno-Vargas, A.J. et al. Synthesis of 1,2,3-triazole-linked glycohybrids in the gluco-, gulo-, and allopyranose series. Chem Heterocycl Comp 51, 664–671 (2015). https://doi.org/10.1007/s10593-015-1754-x

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