Synthesis of disulfide surrogate peptides incorporating an ethylene glycol bridge. (8th February 2023)

• Record Type: Journal Article
• Authors: Wei, Xiao-Xiong; Cui, Ji-Bin; Zhao, Rui; Luo, Jie; Li, Yi-Ming; Bierer, Donald; Shi, Jing
• Is Part Of: New journal of chemistry. Volume 47:Number 9(2023)
• Page Start: 4213
• Page End: 4217
• Publication Date: 2023-02-08
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj05290c
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : We report a new diaminodiacid containing an ethylene glycol bridge for the synthesis of disulfide surrogate peptides. 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.