Development of transition state analogue inhibitors for N-acetylglycosyltransferases bearing D-psicoor D-tagatofuranose scaffolds.

Autor: Baráth, Marek, Lin, Chun-Hung, Tvaroška, Igor, Hirsch, Ján
Zdroj: Chemical Papers; Feb2015, Vol. 69 Issue 2, p348-357, 10p
Abstrakt: New potential transition state analogue inhibitors for N-acetylglucosyltransferases (GnTs) were synthesised. These compounds based on psico- and tagatofuranose (structure) scaffold contained a 2-thiophenyl-1-O-diethylphosphate moiety mimicking the proposed model of the transition state of the enzymatic reaction catalysed by N-acetylglucosyltransferases. The synthesised compounds as well as their precursors were fully characterised by NMR, optical rotation and mass techniques. Anomeric configuration of tagatofuranose derivatives was confirmed by X-ray crystallography. Two types of potential human glycosyltransferase (GnTs) inhibitors representing donor UDP-GlcNAc, assigned for biological assays on human GnTs, were prepared. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index