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Oxime ligation in acetic acid: efficient synthesis of aminooxy‐peptide conjugates
Author(s) -
Chelushkin Pavel S.,
Leko Maria V.,
Dorosh Marina Yu,
Burov Sergey V.
Publication year - 2017
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.2931
Subject(s) - oxime , bioconjugation , chemistry , conjugate , peptide , acetic acid , ligation , combinatorial chemistry , chemical ligation , peptide synthesis , aldehyde , organic chemistry , biochemistry , catalysis , mathematical analysis , mathematics , microbiology and biotechnology , biology
Oxime ligation is a powerful tool in various bioconjugation strategies. Nevertheless, high reaction rates and quantitative yields are typically reported for aldehyde‐derived compounds. In contrary, keto groups react much slower, with quantitative yields achieved at 5 h for low‐molecular weight compounds and more than 15 h for polymers or dendrimers. In this communication, we report that oxime ligation proceeds rapidly with quantitative (>95%) conversion within 1.5–2 h in pure acetic acid. The practical utility of suggested technique is illustrated by the synthesis of peptide‐steroid and peptide‐polymer conjugates of model aminooxy‐peptides. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.