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Aziridine Based Electrophilic Handle for Asparatic Acid Ligation

Abstract

A one-pot ligation strategy at aspartic acid junction has been developed by successfully incorporating aziridin-2,3-dicarboxylate to the N-side of a peptide fragment, affording N-aziridine appended peptide, which was ligated in solution phase with a variety of small peptide thio acids to afford native peptides, following ring-opening/peptidyl migration/desulfurization strategy. The reaction proceeds in 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 aziridine based ligation. Computational studies have also been performed to get insight about the reaction pathway.

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Publication details

The article was received on 20 Mar 2018, accepted on 16 May 2018 and first published on 16 May 2018


Article type: Paper
DOI: 10.1039/C8OB00676H
Citation: Org. Biomol. Chem., 2018, Accepted Manuscript
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    Aziridine Based Electrophilic Handle for Asparatic Acid Ligation

    K. Bajaj, D. S. Agarwal, R. SAKHUJA and G. G. Pillai, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8OB00676H

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