Abstract
To confirm the potential usefulness of amino acid residues as the protecting group of sugar hydroxyls, N-(benzyloxycarbonyl) and -N-(t-butoxycarbonyl) amino acids were condensed with methyl 4, 6-O-benzylidene-α-D-glucopyranoside (1) and methyl 2, 3-di-O-methyl-α-D-glucopyranoside (2), and the conditions were studied for the removal of aminoacyl groups from sugar moieties. The aminoacyl groups were easily removed by enzymatic hydrolysis using pronase E, trypsin and chymotrypsin, as well as alkaline treatment as with conventional acyls. We determined the utility of aminoacyl sugars as new protecting groups having some useful characteristics which never exist in normal circumstances.
