Open Access Open Access  Restricted Access Subscription Access

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

Jevgeņija Uzuleņa, Vitālijs Rjabovs, Antonio J. Moreno-Vargas, Māris Turks
Cover Image

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


Keywords


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

Full Text: PDF Supplementary File(s): SUPPLEMENTARY INFORMATION (3MB)


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv