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Issue 28, 2019
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Synthesis and evaluation of photo-activatable β-diarylsydnone-l-alanines for fluorogenic photo-click cyclization of peptides

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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.

Graphical abstract: Synthesis and evaluation of photo-activatable β-diarylsydnone-l-alanines for fluorogenic photo-click cyclization of peptides

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Publication details

The article was received on 18 Apr 2019, accepted on 25 Jun 2019 and first published on 26 Jun 2019


Article type: Communication
DOI: 10.1039/C9OB00898E
Org. Biomol. Chem., 2019,17, 6777-6781

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    Synthesis and evaluation of photo-activatable β-diarylsydnone-L-alanines for fluorogenic photo-click cyclization of peptides

    Z. Yao, X. Wu, X. Zhang, Q. Xiong, S. Jiang and Z. Yu, Org. Biomol. Chem., 2019, 17, 6777
    DOI: 10.1039/C9OB00898E

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