Microwave-assisted reaction of glycosylamine with aspartic acid.
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.
Laboratory of Peptide and Protein Chemistry and Biology, Polo Scientifico e Tecnologico, University of Firenze, 50019, Sesto Fiorentino, FI, Italy.
Feliciana
F
Real-Fernández
Francesca
F
Nuti
M Angeles
MA
Bonache
Marco
M
Boccalini
Stefano
S
Chimichi
Mario
M
Chelli
Anna Maria
AM
Papini
D000588:Amines / Q000737:chemistry* / Q000528:radiation effects; D001224:Aspartic Acid / Q000528:radiation effects*; D005944:Glucosamine / Q000031:analogs & derivatives / Q000737:chemistry / Q000528:radiation effects; D006031:Glycosylation; D008872:Microwaves; D019906:Nuclear Magnetic Resonance, Biomolecular
D000588:Amines; D001224:Aspartic Acid; C075822:glucopyranosylamine; D005944:Glucosamine