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-alpha-D-allopyranosyl beta-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.
Anders
Jan
J
Carbohydrate Technology, Technical University, Langer Kamp 5, D 38106 Braunschweig, Germany.
Buczys
Rachel
R
Lampe
Elmar
E
Walter
Martin
M
Yaacoub
Emile
E
Buchholz
Klaus
K
D000586:Amination; D000596:Amino Acids / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019904:Polymethyl Methacrylate / Q000737:chemistry*; D013395:Sucrose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013549:Sweetening Agents / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D004187:Disaccharides; D013549:Sweetening Agents; C059956:3-ketosucrose; C048724:allosucrose; D013395:Sucrose; D019904:Polymethyl Methacrylate