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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,Karine Farbiarz,Maria Matveenko,Hanspeter Kählig,Christian F. W. Becker
Organic & Biomolecular Chemistry Pub Date : 06/02/2016 00:00:00 , DOI:10.1039/C6OB00932H
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.

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