Regenerative labeling of saccharides

Abstract

A simple method for regenerative labeling of saccharides is devised by using (naphth-2-ylmethoxy)amine or N-methyl-(naphth-2-ylmethoxy)amine. The naphthyl group is optically responsive to facilitate the separation of labeled saccharides, which are subsequently reverted to the parental saccharides by one-pot hydrogenolysis–hydrolysis using co-catalysts Pd(OH)₂ and HCl under an atmosphere of H₂. The mechanistic study indicates that the naphthylmethyl group plays an essential role in the initial hydrogenolysis, followed by in situ hydrolysis, to regenerate the saccharides.