Catalysis of Hydrazone and Oxime Peptide Ligation by Arginine

23 September 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

Schiff's bases
Hydrazone
Oxime
hydrazide
alpha-oxo aldehyde
peptide
protein
protein aggregation
arginine
nucleophilic catalysis
side-chain assistance
water
phosphate buffer
bicarbonate
CO2
neutral pH
kinetic analysis
glyoxylyl group
conjugate synthesis
Western blot assays

Supplementary materials

Title
Description
Actions
Title
Supplementary Information 6
Description
Actions

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