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Chemoselective Oxime Reactions in Proteins and Peptides by Using an Optimized Oxime Strategy: The Demise of Levulinic Acid
Author(s) -
Agten Stijn M.,
Suylen Dennis,
Ippel Hans,
Kokozidou Maria,
Tans Guido,
van de Vijver Pieter,
Koenen Rory R.,
Hackeng Tilman M.
Publication year - 2013
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201300598
Subject(s) - demise , oxime , levulinic acid , chemistry , ketone , yield (engineering) , organic chemistry , combinatorial chemistry , computer science , world wide web , catalysis , political science , materials science , law , metallurgy
Selecting the right partner faster: In protein chemoselective conjugation, the use of levulinic acid for ketone introduction leads to slow oxime formation and poor yield because of internal cyclization, especially at low concentrations. A mechanism for cyclization is proposed and alternative keto‐acids have been tested. These showed faster formation of oximes without side products.