Affiliation:
1. Udmurt State University
Abstract
The performed condensation of p-aminobenzoic acid with D-mannose produced N-mannopyranosylamine with ? configuration at the anomeric centre, which was confirmed by vibrational spectroscopy. The reactivity of the synthesized product in the processes of acid hydrolysis and thermal oxidation in a freely aerated medium was studied. A hydrolytic stability study showed p-(N-β-D-mannopyranosyl)- aminobenzoic acid, which is stable in ethanolic media, to gradually hydrolyse upon heating (50 °C) in acidic aqueous solutions, as confirmed by FTIR spectroscopy and thin-layer chromatography. Upon thermal oxidation, the synthesized product shows sufficient stability when heated up to 30–50 °C. However, a further increase in temperature to 70 °C accelerates destruction, which is manifested in an increase in the band intensity of 1690 cm-1 (vO=C–C=N) in the spectra of the second derivatives of thermostated samples. This process is assumed to involve direct oxidation of N-glycosylamine, most likely in the acyclic form of enaminol. Additionally, the nature of N-glycosylation by-products was studied by electron and oscillatory spectroscopy. These studies indicated the formation of melanoids – coloured products of deep destruction, which might exhibit growth-regulating and other types of biological activity. The main structural fragments of melanoids are assumed to be formed in solutions through the interaction of enaminol forms with α-dicarbonyl derivatives. Our experimental data obtained earlier also indicate the biological activity of melanoids in arylaminocarbonyl reactions, thereby allowing the technology of obtaining functional products of different stages of sugar-amine interactions to be combined within a single synthesis operation. The feasibility of this approach is determined by the availability of reagents, mild synthesis and product separation conditions, as well as by their environmental friendliness.
Publisher
Irkutsk National Research Technical University
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