Synthesis and evaluation of photo-activatable β-diarylsydnone-l-alanines for fluorogenic photo-click cyclization of peptides. Issue 28 (3rd July 2019)

• Record Type: Journal Article
• Authors: Yao, Zhuojun; Wu, Xueting; Zhang, Xiaocui; Xiong, Qin; Jiang, Shichao; Yu, Zhipeng
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 28(2019)
• Page Start: 6777
• Page End: 6781
• Publication Date: 2019-07-03
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob00898e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : β-Diarylsydnone-l -alanines were designed and introduced into peptides allowing photo-cyclization only in phosphate containing buffer with concomitant fluorescence generation in live cells. Abstract : Herein, we design and synthesize a series of photoactivatable β-diarylsydnone-l -alanines (DASAs), which have excellent photo-reactivity with high fluorescence turn-on toward alkenes in a biocompatible environment. The environmental sensing properties of the resulting fluorescent pyrazoline-alanine facilitate its probing capability. By introducing the DASA residue on the side chain of linear peptides, the macrocyclic peptides resulting from the in situ photo-cyclization toward the alkene residue exhibited fluorogenic translocation through live cell membranes.