The Journal of Biological Physics and Chemistry

N-glycosylation of aminobenzoic acids by galactose and rhamnose

R. Kublashvili¹, M. Labartkava¹, and D. Ugrekhelidze²

¹ Department of Chemistry, I. Javakhishvili Tbilisi State University, 0128 Tbilisi, Georgia
² Durmishidze Institute of Biochemistry and Biotechnology, Georgian Academy of Sciences, David Agmashenebeli Allée 10 km, 0159 Tbilisi, Georgia

The N-glycosylation of o-, m- and p-aminobenzoic acids by D-galactose and L-rhamnose 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 aminobenzoic acids, an anomeric effect is observed: N-o-carboxyphenyl-D-galactosylamine and N-p-carboxyphenyl-L-rhamnosylamine appear only as β-anomers, and the other N-carboxyphenyl-D-galactosylamines and N-carboxyphenyl-L-rhamnosylamines appear as a mixture of α- and β-anomers. The transformation of synthesized N-glycosides into melanoidins is also investigated.

Keywords: aminobenzoic acids, D-galactose, L-rhamnose, melanoidins, N-glycosides