Issue 9, 2023

Synthesis of disulfide surrogate peptides incorporating an ethylene glycol bridge

Abstract

The replacement of disulfide bonds with metabolically stable isosteres by a diaminodiacid strategy has been demonstrated as an effective and flexible method to improve the stability of disulfide-rich peptides. In this study, we report a new diaminodiacid containing ethylene glycol bridge (EG-DADA), obtained primarily through the ring-opening addition reaction of aziridine derivatives with hydroxyl groups. The practicability and oxidation stability of this novel diaminodiacid have been illustrated by the synthesis of disulfide bond mimics of tachyplesin I and α-ImI. The development of EG-DADA enriches the ether-based diaminodiacids and provides a flexible option for the construction of disulfide surrogate peptides.

Graphical abstract: Synthesis of disulfide surrogate peptides incorporating an ethylene glycol bridge

Supplementary files

Article information

Article type
Paper
Submitted
29 okt 2022
Accepted
17 jan 2023
First published
24 jan 2023

New J. Chem., 2023,47, 4213-4217

Synthesis of disulfide surrogate peptides incorporating an ethylene glycol bridge

X. Wei, J. Cui, R. Zhao, J. Luo, Y. Li, D. Bierer and J. Shi, New J. Chem., 2023, 47, 4213 DOI: 10.1039/D2NJ05290C

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