Oxime ligation in acetic acid: efficient synthesis of aminooxy ‐peptide conjugates

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. In this communication, we report that oxime ligation between peptides and keto compounds of different nature 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‐petides.
Source: Journal of Peptide Science - Category: Biochemistry Authors: Tags: Rapid Communication Source Type: research