Heating reactions of N-t-Butyloxycarbonyl-Asparagine and related compounds

Article abstract of DOI:10.14233/ajchem.2014.16493

N-t-Butyloxycarbonyl-amino acids (Boc-) are labile on heating to afford free amino acids, but Boc-aspartic acid gives a kind of polypeptide. This chemical feature of Boc-aspartic acid may be caused by dehydration between two carboxyl groups as well as the formation of a free amino group. Boc-Asparagine may have a similar reactivity to Boc-aspartic acid. This research describes polypeptide formation by heating Boc-asparagine and its isomer Boc-aspartic acid amide.