Synthesis of Uridine-5-propylamine Derivatives and Their Use in Affinity Chromatography of N-Acetylglucosaminyltransferases I and II.

Abstract The C-5 substituted uridine derivatives UDP-5-propylamine ( 7 ) and UDP-GlcNAc-5-propylamine ( 8 ) were synthesized in good yields by Heck alkylation of the 5-mercuriuridines, followed by hydrogenation. The products were characterized by 1 H and 13 C NMR spectroscopy, electrospray mass spectrometry and UV spectrophotometry. The amines are of interest for the preparation of affinity probes for glycosyltransferases. The benzoylbenzamides of 7 and 8 show strong competitive inhibition of N -acetylglucosaminyltransferases I and II with K i values ranging from 30 to 100 μM (without irradiation) and may be useful as active site-directed photoaffinity labels. A conjugate of 8 and Sepharose was used for affinity chromatographic purification of N -acetylglucosaminyltransferases I and II. The results indicate that this affinity gel is a stable alternative to the commonly used but unstable UDP-GlcNAc-5-Hg-thiopropyl conjugate.