Volume 4, Number 3, p. 169–173
N-glycosylation of aminophenols by mannose, rhamnose and maltose
R. Kublashvili,1 M. Labartkava1 and D. Ugrekhelidze2
1Department of Chemistry, I. Javakhishvili Tbilisi State University, Tbilisi 0128, Georgia
2Institute of Biochemistry and Biotechnology, Georgian Academy of Sciences
The N-glycosylation of o-, m- and p-aminophenols by mannose, rhamnose and maltose is described. The composition of the synthesized products is established by microchemical analysis, and their IR and 13C nmr spectra are investigated. As a result of the N-glycosylation of isomeric aminophenols, the anomeric effect is observed: N-o-hydroxyphenylmannosylamine and N-o-hydroxyphenylrhamnisylamine appear only as b-anomers, and the other N-hydroxyphenyl-glycosylamines appear as a mixture of a- and b-anomers.
Key words: aminophenols, maltose, mannose, N-glycosides, rhamnose