Strategic Alkene Incorporation into Peptide Backbones to Prevent Enzymatic Hydrolysis by Evading Molecular Recognition

Kohei Watanabe; Yoshinori Taguchi; Takuma Nishizawa; Sayuri Takeo; Chihiro Iio; Nobuyuki Mase; Kohei Sato; Tetsuo Narumi

doi:10.1039/d5cc07071f

January 1, 2026Chemical Communications

Strategic Alkene Incorporation into Peptide Backbones to Prevent Enzymatic Hydrolysis by Evading Molecular Recognition

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Key Points

The research aims to demonstrate how replacing specific peptide bonds with alkene isosteres can enhance the stability of peptides against enzymatic degradation.
Modification of the peptide backbone at the C-terminal region of ubiquitin
Replacement of Gly75-Gly76 bond with alkene dipeptide isosteres
Evaluation of resistance to hydrolysis by enzymatic assays
Alkene dipeptide isosteres significantly increased the resistance to enzymatic hydrolysis compared to traditional peptides
Enhanced stability observed specifically at the C-terminal region of ubiquitin

Implication

Novel alkene modifications aim to evade enzymatic hydrolysis in peptides, suggesting improved stability.

Abstract

This study highlighted a novel utility of alkene dipeptide isosteres in peptide backbone modification, specifically at the C-terminal region of ubiquitin. By strategically replacing the Gly75-Gly76 peptide bond with these...

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Cite This Study

Watanabe et al. (2026) studied this question.

synapsesocial.com/papers/69d894ce6c1944d70ce05c9e https://doi.org/10.1039/d5cc07071f

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Strategic Alkene Incorporation into Peptide Backbones to Prevent Enzymatic Hydrolysis by Evading Molecular Recognition

Key Points

Implication

Abstract

Discussion

Cite This Study

Strategic Alkene Incorporation into Peptide Backbones to Prevent Enzymatic Hydrolysis by Evading Molecular Recognition

Key Points

Implication

Abstract

Discussion

Cite This Study

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