Journal
ORGANIC LETTERS
Volume 22, Issue 21, Pages 8608-8612Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03195
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Funding
- CNRS
- INSERM
- Institut Pasteur de Lille
- University of Lille
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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 a nucleophilic catalyst and a protein aggregation inhibitor, arginine hydrochloride is a useful addition to the hydrazone/oxime ligation toolbox.
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