New regioselective derivatives of sucrose with amino acid and acrylic groups

We report here a range of new sucrose derivatives obtained from ‘3-ketosucrose’ in aqueous medium with few reaction steps. As an intermediate, 3-amino-3-deoxy-α-d-allopyranosyl β-d-fructofuranoside (1) was obtained via the classical route of reductive amination with much improved yield and high stereoselectivity. Building blocks for polymerization were synthesized by introduction of acrylic-type side chains, for example, with methacrylic anhydride. Corresponding polymers were synthesized. Aminoacyl and peptide conjugates were obtained through conventional peptide synthesis with activated and protected amino acids. Deprotection yielded new glycoderivatives having an unconventional substitution pattern, namely 3-(aminoacylamino) allosaccharides. Both mono- and di-peptide conjugates of allosucrose have been synthesized.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide