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Publikācija: Synthesis of Novel 3-Deoxy-3-C-Triazolylmethyl-Allose Derivatives and Evaluation of Their Biological Activity

Publication Type Publication (anonimusly reviewed) in a journal with an international editorial board indexed in other databases
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language Synthesis of Novel 3-Deoxy-3-C-Triazolylmethyl-Allose Derivatives and Evaluation of Their Biological Activity
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Jekaterina Rjabova
Vitālijs Rjabovs
Antonio José Moreno Vargas
Elena Moreno Clavijo
Māris Turks
Keywords 3-deoxy-3-C-triazolylmethyl-allose; methylene linker; triazolyl-monosaccharides; click chemistry, inhibitors of glycosidases
Abstract Recently, monosaccharide-triazole conjugates have proved to possess a large variety of useful biological activities. This paper describes synthesis of a new series of 3-deoxy-3-C-triazolylmethyl-allose derivatives. These latter are obtained from acetonide-protected 3-deoxy-3-azidomethyl allose and commercial alkynes via Cu(I) catalyzed 1,3-dipolar cycloaddition. The obtained molecular scaffolds differ from those described earlier by methylene linker (-CH2-) between the C(3) of allose and triazole moiety. It was demonstrated that acetonide-protected monosaccharide, 3-deoxy-3-C-(4-phenyl-1H-1,2,3-triazol-1-yl)methyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose, inhibited α-L-fucosidase for 26% at 0.1 mM concentration, but a deprotected analog, 3-deoxy-3-C-(4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl)methyl-β-D-allofuranose, showed 15% inhibition of β-glucosidase at 1 mM concentration.
DOI: 10.2478/s11532-012-0002-9
Hyperlink: http://www.springerlink.com/content/x29005l152m31671/ 
Reference Rjabova, J., Rjabovs, V., Moreno Vargas, A., Moreno Clavijo, E., Turks, M. Synthesis of Novel 3-Deoxy-3-C-Triazolylmethyl-Allose Derivatives and Evaluation of Their Biological Activity. Central European Journal of Chemistry, 2012, Vol.10, Iss.2, pp.386-394. e-ISSN 1644-3624. ISSN 1895-1066. Available from: doi:10.2478/s11532-012-0002-9
ID 12727