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Catalysis of Hydrazone and Oxime Peptide Ligation by Arginine

preprint
revised on 16.10.2020 and posted on 16.10.2020 by Nathalie Ollivier, Vangelis Agouridas, Benoît Snella, Rémi Desmet, Hervé Drobecq, Jérôme Vicogne, Oleg Melnyk
Hydrazone and oxime peptide ligations are catalyzed by arginine. The catalysis is assisted intramolecularly by the side-chain guanidinium group. Hydrazone ligation in the presence of arginine proceeds efficiently in phosphate buffer at neutral pH but is particularly powerful in bicarbonate/CO2 buffer. In addition to acting as a catalyst, arginine prevents the aggregation of proteins during ligation. With its dual properties as nucleophilic catalyst and protein aggregation inhibitor, arginine hydrochloride is a useful addition to the hydrazone/oxime ligation toolbox.

History

Email Address of Submitting Author

oleg.melnyk@ibl.cnrs.fr

Institution

CNRS

Country

France

ORCID For Submitting Author

0000-0002-3863-5613

Declaration of Conflict of Interest

The authors declare no conflict of interest

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