Issue 2, 2023, Issue in Progress

Design and synthesis of a clickable, photoreactive amino acid p-(4-(but-3-yn-1-yl)benzoyl)-l-phenylalanine for peptide photoaffinity labeling

Abstract

Photoaffinity labeling is a powerful technique to investigate the interactions between bioactive peptides and their targets. To construct a peptide-derived photoaffinity probe, at least two amino acids need to be modified or replaced, increasing experimental difficulties and negatively affecting activity. Herein, we report the synthesis of a clickable, photoreactive amino acid p-(4-(but-3-yn-1-yl)benzoyl)-L-phenylalanine (Abpa) and its Fmoc-protected version from 3-(4-bromophenyl)-1-propanol in 11 steps with an overall 12.5% yield. The amino acid contains both a photoreactive benzophenone and a clickable terminal alkyne which acts like a reporter tag by fast attachment to other functional groups via ‘click’ reaction, and a photoaffinity probe could be created by one single amino acid substitution during peptide synthesis. And its small size helps to retain bioactivity. The efficiency of Abpa was demonstrated by photoaffinity labeling experiments using photoactivatable probes of α-conotoxin MI.

Graphical abstract: Design and synthesis of a clickable, photoreactive amino acid p-(4-(but-3-yn-1-yl)benzoyl)-l-phenylalanine for peptide photoaffinity labeling

Supplementary files

Article information

Article type
Paper
Submitted
15 Nov 2022
Accepted
17 Dec 2022
First published
04 Jan 2023
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2023,13, 866-872

Design and synthesis of a clickable, photoreactive amino acid p-(4-(but-3-yn-1-yl)benzoyl)-L-phenylalanine for peptide photoaffinity labeling

P. Han, F. Wang, S. Bao, G. Yao, X. Wan, J. Liu and H. Jiang, RSC Adv., 2023, 13, 866 DOI: 10.1039/D2RA07248C

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