Issue 30, 2024

Unexpected diselenide metathesis in selenocysteine-substituted biologically active peptides

Abstract

Substitution of disulfide bonds with a diselenide bonds in peptides and proteins is an often-used strategy to increase the stability of naturally occurring peptides and proteins. In this paper, diselenide metathesis between model diselenide dimer peptides, as well as that in diselenide(s)-substituted biologically active peptides, were analyzed. Surprisingly, depending on the tertiary structure of the peptides, we observed that the metathesis reaction occurs under physiological conditions even in the absence of reducing agents, light and heating.

Graphical abstract: Unexpected diselenide metathesis in selenocysteine-substituted biologically active peptides

Supplementary files

Article information

Article type
Communication
Submitted
31 May 2024
Accepted
02 Jul 2024
First published
04 Jul 2024

Org. Biomol. Chem., 2024,22, 6108-6114

Unexpected diselenide metathesis in selenocysteine-substituted biologically active peptides

Y. He, T. Takei, L. Moroder and H. Hojo, Org. Biomol. Chem., 2024, 22, 6108 DOI: 10.1039/D4OB00921E

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