Enzymatic synthesis of amino acid-sugar alcohol conjugates in organic media

Abstract

Amino acid-sugar alcohol conjugates were synthesized by a commercial serine protease, Optimase M-440, in organic media. Optimase M-440 showed broad substrate specificity towards N-t-Boc-protected L-amino acids as acyl donors and sugar alcohols as nucleophiles. Among various solvents tested Optimase M-440 showed the highest activity in pyridine. The regioselective acylation of the primary -OH groups of sugar alcohols gave the amino acid conjugates in good yields without byproducts.