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

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

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

11 Citations (Web of Science)

Abstract

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.
Original languageEnglish
Pages (from-to)2431-2434
JournalChembiochem
Volume14
Issue number18
DOIs
Publication statusPublished - 16 Dec 2013

Keywords

  • bioconjugation
  • ketones
  • oximes
  • peptides
  • RANTES

Cite this