Arginine side-chain modification that occurs during copper-catalysed azide–alkyne click reactions resembles an advanced glycation end product

Anne C. Conibear; Karine Farbiarz; Rupert L. Mayer; Maria Matveenko; Hanspeter Kählig; Christian F. W. Becker

doi:10.1039/C6OB00932H

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Arginine side-chain modification that occurs during copper-catalysed azide–alkyne click reactions resembles an advanced glycation end product†

Anne C. Conibear,

^a Karine Farbiarz,^a Rupert L. Mayer,

^bc Maria Matveenko,^a Hanspeter Kählig^d and Christian F. W. Becker*^a

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* Corresponding authors

^a University of Vienna, Faculty of Chemistry, Institute of Biological Chemistry, Währinger Straße 38, 1090 Vienna, Austria
E-mail: christian.becker@univie.ac.at
Fax: +43 1 4277 870510
Tel: +43 1 4277 70510

^b University of Vienna, Faculty of Chemistry, Institute of Analytical Chemistry, Währinger Straße 38, 1090 Vienna, Austria

^c University of Vienna, Faculty of Chemistry, Mass Spectrometry Centre, Währinger Straße 38, 1090 Vienna, Austria

^d University of Vienna, Faculty of Chemistry, Institute of Organic Chemistry, Währinger Straße 38, 1090 Vienna, Austria

Abstract

Dehydroascorbate is a by-product of copper-catalysed azide–alkyne click (CuAAC) reactions and also forms advanced glycation end products (AGEs) in tissues undergoing oxidative stress. Here we isolate and characterize an arginine–dehydroascorbate adduct formed during CuAAC reactions, investigate strategies for preventing its formation, and propose its biological relevance as an AGE.

This article is part of the themed collection: Selective Chemistry with Peptides and Proteins

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Article information

DOI: https://doi.org/10.1039/C6OB00932H
Article type: Communication
Submitted: 29 Apr 2016
Accepted: 01 Jun 2016
First published: 02 Jun 2016

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Org. Biomol. Chem., 2016,14, 6205-6211

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Arginine side-chain modification that occurs during copper-catalysed azide–alkyne click reactions resembles an advanced glycation end product

A. C. Conibear, K. Farbiarz, R. L. Mayer, M. Matveenko, H. Kählig and C. F. W. Becker, Org. Biomol. Chem., 2016, 14, 6205 DOI: 10.1039/C6OB00932H

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Organic & Biomolecular Chemistry

Arginine side-chain modification that occurs during copper-catalysed azide–alkyne click reactions resembles an advanced glycation end product†

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Arginine side-chain modification that occurs during copper-catalysed azide–alkyne click reactions resembles an advanced glycation end product

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