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Issue 23, 2018
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Aziridine based electrophilic handle for aspartic acid ligation

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Abstract

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.

Graphical abstract: Aziridine based electrophilic handle for aspartic acid ligation

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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., 2018,16, 4311-4319
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    Aziridine based electrophilic handle for aspartic acid ligation

    K. Bajaj, D. S. Agarwal, R. Sakhuja and G. G. Pillai, Org. Biomol. Chem., 2018, 16, 4311
    DOI: 10.1039/C8OB00676H

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