Synthesis of Aldose 11‐Mercaptoundecanoyl Hydrazones as Promising Glycoligands of Noble Metal Nanoparticles

Abstract

Thesynthetic method for previously unknown 11-mercaptoundecanoyl hydrazones of the aldose series (L-arabinose, D-ribose, D-xylose, L-rhamnose, L-fucose, D-mannose, D-galactose, Dglucose, N-acetyl-D-glucosamine, N-acetyl-D-mannosamine, Dlactose, D-maltose) was developed, and structures of the productes were determined. These compounds are perspective glycoligands for noble metal nanoparticles. The 1 H and 13 C NMR spectroscopy data show that most of these aldose 11mercaptoundecanoyl hydrazones in DMSO-d 6 solution exist as a tautomeric mixture of open hydrazone and cyclic pyranose forms. The linear hydrazone form is represented by a set of Z',E'-conformational isomers, differing in the arrangement of substituents relative to the amide bond C-N, in comparable amounts. In the case of 11-mercaptoundecanoyl hydrazones derived from D-glucose, D-lactoseand D-maltose, the cyclic pyranose structure represented by α,β-configurational isomers is retained.