Microwave-assisted reaction of glycosylamine with aspartic acid

Amino Acids. 2010 Jul;39(2):599-604. doi: 10.1007/s00726-010-0484-8. Epub 2010 Feb 4.

Abstract

The synthesis of N-protected glycosyl amino acids from amines has been investigated and it was found that, under microwave conditions, glycosylamines could be hydrolyzed leading to new products containing a glycosyl ester linkage. The efficiency of the microwave-induced glycosylation of aspartic acid was studied comparing the microwave activity between amide and ester bond formation. Different sugar moieties have been employed to demonstrate the simple and reproducible coupling methodology. New glycosyl ester compounds were further characterized by NMR spectroscopy.

MeSH terms

  • Amines / chemistry*
  • Amines / radiation effects
  • Aspartic Acid / radiation effects*
  • Glucosamine / analogs & derivatives
  • Glucosamine / chemistry
  • Glucosamine / radiation effects
  • Glycosylation
  • Microwaves*
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • Amines
  • Aspartic Acid
  • glucopyranosylamine
  • Glucosamine