Solid-phase Fluorescent BODIPY-peptide Synthesis Dipyrrin Construction

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Jun 7

PMID 34094367

Citations 11

Authors

Yue Wu

Wing-Sze Tam

Ho-Fai Chau

Simranjeet Kaur

Waygen Thor

Wei Shen Aik

Wai-Lun Chan

Markus Zweckstetter

Ka-Leung Wong

Affiliations

Soon will be listed here.

Abstract

Traditional fluorescent peptide chemical syntheses hinge on the use of limited fluorescent/dye-taggable unnatural amino acids and entail multiple costly purifications. Here we describe a facile and efficient protocol for construction of dipyrrins on the N-terminus with 20 natural and five unnatural amino acids and the lysine's side chain of selected peptides/peptide drugs through Fmoc-based solid-phase peptide synthesis. The new strategy enables the direct formation of boron-dipyrromethene (BODIPY)-peptide conjugates from simple aldehyde and pyrrole derivatives without pre-functionalization, and only requires a single-time chromatographic purification at the final stage. As a model study, synthesized EBNA1-targeting demonstrates intact selectivity , responsive fluorescence enhancement, and higher light cytotoxicity due to the photo-generation of cytotoxic singlet oxygen. This work offers a novel practical synthetic platform for fluorescent peptides for multifaceted biomedical applications.

Citing Articles

Noncanonical Amino Acids in Biocatalysis.

Birch-Price Z, Hardy F, Lister T, Kohn A, Green A Chem Rev. 2024; 124(14):8740-8786.

PMID: 38959423 PMC: 11273360. DOI: 10.1021/acs.chemrev.4c00120.

Acid-Resistant BODIPY Amino Acids for Peptide-Based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets.

Mendive-Tapia L, Miret-Casals L, Barth N, Wang J, De Bray A, Beltramo M Angew Chem Weinheim Bergstr Ger. 2024; 135(20):e202302688.

PMID: 38516305 PMC: 10952496. DOI: 10.1002/ange.202302688.

Rationales Design von Phe-BODIPY-Aminosäuren als fluorogene Bausteine für den peptidbasierten Nachweis von -Infektionen im Harntrakt.

Mendive-Tapia L, Mendive-Tapia D, Zhao C, Gordon D, Benson S, Bromley M Angew Chem Weinheim Bergstr Ger. 2024; 134(17):e202117218.

PMID: 38505242 PMC: 10946803. DOI: 10.1002/ange.202117218.

Acid-Resistant BODIPY Amino Acids for Peptide-Based Fluorescence Imaging of GPR54 Receptors in Pancreatic Islets.

Mendive-Tapia L, Miret-Casals L, Barth N, Wang J, De Bray A, Beltramo M Angew Chem Int Ed Engl. 2023; 62(20):e202302688.

PMID: 36917014 PMC: 10947197. DOI: 10.1002/anie.202302688.

Incorporation of Non-Canonical Amino Acids into Antimicrobial Peptides: Advances, Challenges, and Perspectives.

Du Y, Li L, Zheng Y, Liu J, Gong J, Qiu Z Appl Environ Microbiol. 2022; 88(23):e0161722.

PMID: 36416555 PMC: 9746297. DOI: 10.1128/aem.01617-22.

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