SYNTHESIS OF 1,2,3-TRIAZOLE-LINKED GLYCOHYBRIDS IN THE GLUCO-, GULO-, AND ALLOPYRANOSE SERIES

Authors

  • Jevgeņija Uzuleņa Institute of Technology of Organic Chemistry, Riga Technical University
  • Vitālijs Rjabovs Institute of Technology of Organic Chemistry, Riga Technical University
  • Antonio J. Moreno-Vargas Department of Organic Chemistry, Faculty of Chemistry, University of Seville
  • Māris Turks Institute of Technology of Organic Chemistry, Riga Technical University

DOI:

https://doi.org/10.1007/2546

Keywords:

allose, glucose, gulose, 1, 2, 3-triazole, click chemistry, extended bistriazolyl linker, furanose–pyranose equilibrium, galactosidase activators

Abstract

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-[(1,2,3-1H-triazol-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.

How to Cite
Uzuleņa, J.; Rjabovs, V.; Moreno-Vargas, A. J.; Turks, M. Chem. Heterocycl. Compd. 2015, 51, 664. [Khim. Geterotsikl. Soedin. 2015, 51, 664.]

For this article in the English edition see DOI 10.1007/s10593-015-1754-x

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Published

2015-07-31

Issue

Vol. 51 No. 7 (2015)

Section

Original Papers