dr Barbara Dmochowska
dr Barbara Dmochowska :: Research Topics
dr Barbara Dmochowska
glycosyl and glycoammonium salts
Czwartorzędowe sole amoniowe powstają w wyniku nukleofilowego ataku trzeciorzędowej aminy na halogenek alkilu. Reakcję taką nazywamy reakcją Menschutkina.
Treating per-O-acetylglycopyranosyl halide and per-O-acetyl-6-O-tosyl (or 6-deoxy-6-iodo) alkyl/aryl glycopyranoside as R−X analogues in the Menschutkin reaction, a number of reactions for the formation of glycosyl and glycoammonium salts on preparative and micro scale with aliphatic and aromatic amines were carried out in our plant.
Suitable quaternary ammonium salts of nucleosides appear to be the most promising in the search for bactericidal, viral and fungicidal compounds.
Preparation of the 5'-O-tosyl derivative of thymidine and uridine (nucleosides) allowed the derivatives to be converted into quaternary ammonium salts:
Quaternary ammonium salts containing one sugar residue have been tested for their biological activity because, as analogues of naturally occurring compounds, they are non-toxic, readily biodegradable, and the presence of a full positive charge conditions their penetration through the cell wall.
Previous biological studies (within cooperation with the Medical University of Gdańsk) have shown that two salts: N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-trimethylammonium bromide and N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)pyridinium bromide exhibit a pronounced non-competitive inhibitory activity (respective EC50% = 0.05 and 0.5 mM) against AM deaminase. (AMD-DA) isolated from rat skeletal muscle.
Preliminary experimental results regarding the biological activity of quaternary glycosyl- and glycopyranosyl-ammonium salts lead us to design and implement further syntheses, as well as studies of other chemical transformations:
- synthesis of di- and triammonium systems,
- synthesis of more complex compounds containing, inter alia, ester-attached fatty acid residues,
- studies of the pathways of synthesized salts in the Hofman elimination reaction,
- thermogravimetric tests,
- further testing of biological activity.