Liu C F, Tam J P
Department of Microbiology and Immunology, A-5116, MCN, Nashville, Tennessee 37232-2363, USA.
Org Lett. 2001 Dec 27;3(26):4157-9. doi: 10.1021/ol0167614.
We describe an efficient enzymatic approach to the synthesis of amino acid and peptide esters. The serine protease subtilisin Carlsberg (EC 3.4.21.62) was found to efficiently catalyze the specific formation of C(alpha)-carboxyl 3-hydroxypropyl or 4-hydroxybutyl esters of certain Boc-amino acids and peptides in high-content 1,3-propanediol or 1,4-butanediol solution, with substrate specificity parallel to that of the normal hydrolytic reaction. This approach can be coupled with kinetic-control reverse proteolysis in a two-step enzymatic peptide ligation scheme. [reaction: see text]
