These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
Catalysis of Hydrazone and Oxime Peptide Ligation by Arginine
preprintrevised on 16.10.2020, 07:47 and posted on 16.10.2020, 10:41 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.