Cleaving protected peptides from 2-chlorotrityl chloride resin. Moving away from dichloromethane. Issue 9 (17th April 2020)

• Record Type: Journal Article
• Authors: Alhassan, Mahama; Al Musaimi, Othman; Collins, Jonathan M.; Albericio, Fernando; de la Torre, Beatriz G.
• Is Part Of: Green chemistry. Volume 22:Issue 9(2020)
• Page Start: 2840
• Page End: 2845
• Publication Date: 2020-04-17
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d0gc00834f
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : Anisole and 1, 3-dimethoybenzene are excellent alternatives to DCM for cleaving protected peptides. Abstract : In recent years, the work of various research groups has allowed the substitution of the hazardous solvents most widely used in solid-phase peptide synthesis, namely DMF, NMP, DCM, DEE, among others, by several much less hazardous solvents. Indeed, greener alternatives have been found for almost all steps of the process, with the exception of the cleavage of protected peptides from 2-chlorotrityl chloride resin. Here, after careful screening of several of the so-called green solvents, we propose 2% TFA in either anisole or 1, 3-dimethoxybenzene as optimal for the cleavage step. The higher boiling point of these solvents compared with the DCM allows the preparation of protected peptides with less risk of premature removal of the most labile protecting groups, such as the Trt of His. Our findings once again evidence the value/versatility of green solvents in strict chemical terms.