Synthesis and evaluation of photo-activatable β-diarylsydnone-l-alanines for fluorogenic photo-click cyclization of peptides
Literature Information
Publication Date
2019-06-26
DOI
10.1039/C9OB00898E
Impact Factor
3.876
Authors
Zhuojun Yao, Xueting Wu, Xiaocui Zhang, Qin Xiong, Shichao Jiang, Zhipeng Yu
View Original
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.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
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Sodium 6-amino-3-[(E)-{4-[(E)-(4-aminophenyl)diazenyl]-2-methoxy-5-methylphenyl}diazenyl]-4-hydroxy-2-naphthalenesulfonate
CAS Number:
2945-96-2
Molecular Formula:
C24H21N6NaO5S
![9,9'-Spirobi[fluoren]-2-amine structure](https://static.chemtradehub.com/structs/118/118951-68-1-0d14.webp "9,9'-Spirobi[fluoren]-2-amine structure")
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