Arginine side-chain modification that occurs during copper-catalysed azide-alkyne click reactions resembles an advanced glycation end product.
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.
University of Vienna, Faculty of Chemistry, Institute of Biological Chemistry, Währinger Straße 38, 1090 Vienna, Austria. christian.becker@univie.ac.at.
Anne C
AC
Conibear
Karine
K
Farbiarz
Rupert L
RL
Mayer
Maria
M
Matveenko
Hanspeter
H
Kählig
Christian F W
CF
Becker
D000480:Alkynes / Q000737:chemistry*; D001120:Arginine / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry*; D003683:Dehydroascorbic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D017127:Glycation End Products, Advanced / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D000480:Alkynes; D001386:Azides; D017127:Glycation End Products, Advanced; D003300:Copper; D001120:Arginine; D003683:Dehydroascorbic Acid