Issue 8, 2024

The dipicolylamino group as an efficient leaving group for amide bond formation via hexafluoroisopropyl ester

Abstract

Peptide dipicolylamide was prepared by the solid-phase method. The amide was activated by Cu(II) ions in hexafluoroisopropanol and converted to the corresponding active ester. It was condensed with the C-terminal segment to realize segment coupling. The method was successfully applied to the synthesis of an atrial natriuretic peptide and RNase T1.

Graphical abstract: The dipicolylamino group as an efficient leaving group for amide bond formation via hexafluoroisopropyl ester

Supplementary files

Article information

Article type
Paper
Submitted
10 Jan 2024
Accepted
25 Jan 2024
First published
26 Jan 2024

Org. Biomol. Chem., 2024,22, 1699-1707

The dipicolylamino group as an efficient leaving group for amide bond formation via hexafluoroisopropyl ester

Y. Akai, Y. Asahina and H. Hojo, Org. Biomol. Chem., 2024, 22, 1699 DOI: 10.1039/D4OB00045E

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