Aziridine based electrophilic handle for aspartic acid ligation

作者：Bajaj Kiran^*; Agarwal Devesh S; Sakhuja Rajeev; Pillai Girinath G

来源：Organic and Biomolecular Chemistry, 2018, 16(23): 4311-4319.

DOI：10.1039/c8ob00676h

A one-pot ligation strategy at aspartic acid junctions has been developed by successfully incorporating aziridin-2,3-dicarboxylate to the N-side of a peptide fragment, affording N-aziridine appended peptides, which were ligated in solution phase with a variety of small peptide thio acids to afford native peptides, following a ring-opening/peptidyl migration/desulfurization strategy. The reaction proceeds in a highly regiospecific manner, and provides short native peptides in good isolable yields. A variety of aspartame based peptides were synthesized to showcase the generality of this aziridine based ligation. Computational studies have also been performed to obtain insight about the reaction pathway.

• 出版日期2018-6-21