Chemoselective Oxime Reactions in Proteins and Peptides by Using an Optimized Oxime Strategy: The Demise of Levulinic Acid | Zendy

Agten Stijn M. | Zendy; Suylen Dennis | Zendy; Ippel Hans | Zendy; Kokozidou Maria | Zendy; Tans Guido | Zendy; van de Vijver Pieter | Zendy; Koenen Rory R. | Zendy; Hackeng Tilman M. | Zendy

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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.

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