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 Oct 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements