Synthesis of 1,2,3-Triazole-Linked Glycohybrids in the Gluco-, Gulo-, and Allopyranose Series

Химия гетероциклических соединений = Khimiya Geterotsiklicheskikh Soedinenii 2015
Jevgeņija Uzuleņa, Vitālijs Rjabovs, Antonio J. Moreno-Vargas, Māris Turks

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.

Keywords
1,2,3-triazole; allose; click chemistry; extended bistriazolyl linker; furanose–pyranose equilibrium; galactosidase activators; glucose; gulose
Hyperlink
http://hgs.osi.lv/index.php/hgs/article/view/2546

Uzuleņa, J., Rjabovs, V., Moreno-Vargas, A., Turks, M. Synthesis of 1,2,3-Triazole-Linked Glycohybrids in the Gluco-, Gulo-, and Allopyranose Series. Химия гетероциклических соединений = Khimiya Geterotsiklicheskikh Soedinenii, 2015, Vol.51, No.7, pp.664-671. ISSN 0009-3122.

Publication language
English (en)