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Revisiting NO2 as Protecting group of Arginine in Solid-Phase Peptide Synthesis

Lopez, John and Mahama , Alhassan and Kumar, Ashish and Albericio, Fernando and G. de la Torre, Beatriz (2020) Revisiting NO2 as Protecting group of Arginine in Solid-Phase Peptide Synthesis. International journal of molecular sciences, 21 (12). pp. 1-12. ISSN 1422-0067

Abstract

The protection of side-chain arginine in solid-phase peptide synthesis requires attention since current protecting groups have several drawbacks. Herein, the NO2 group, which is scarcely used, has been revisited. This work shows that it prevents the formation of δ-lactam—the most severe side-reaction during the incorporation of Arg. Moreover, it is stable in solution for long periods and can be removed in a friendly manner. Thus, this protecting group can be removed while the protected peptide is still anchored to the resin, using SnCl2 as reducing agent in mild acid conditions using 2-MeTHF as solvent at 55°C Furthermore, we demonstrate that sonochemistry can facilitate the removal of NO2 from multiple Arg-containing peptides.

Item Type: Article
Date Deposited: 05 Jan 2021 00:45
Last Modified: 05 Jan 2021 00:45
URI: https://oak.novartis.com/id/eprint/42683

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