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Greener Cleavage of Protected Peptide Fragments from Sieber Amide Resin

Lookup NU author(s): Dr Othman AlmusaimiORCiD

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

Following the successful introduction of two benign solvents for cleaving protected acid peptide fragments from 2-chlorotrityl chloride (2-CTC) resin, there is a need to green the cleavage process for obtaining protected peptide amide fragments. In this work, p-xylene and toluene are introduced as greener alternates to dichloromethane (DCM) for preparing protected peptide amide fragments from a Sieber amide resin. The N-dealkylation is a demanding chemical reaction, requiring that the cleavage protocol be optimised to ensure complete cleavage from the resin. After a 30 min reaction time, only 66 % of the final peptide product was retrieved even with the conventional dichloromethane solvent. Therefore, 120 min was considered sufficient to fully cleave the peptide from the Sieber amide resin. This work reaffirms the fact that greening strategies are far from detrimental, with green alternatives often outperforming their replaced counterparts.

Publication metadata

Author(s): Al Musaimi O, Gavva V, Williams DR

Publication type: Article

Publication status: Published

Journal: ChemistryOpen

Year: 2022

Volume: 11

Issue: 12

Online publication date: 23/12/2022

Acceptance date: 14/12/2022

Date deposited: 27/02/2024

ISSN (electronic): 2191-1363

Publisher: Wiley

URL: https://doi.org/10.1002/open.202200236

DOI: 10.1002/open.202200236

Data Access Statement: The data that support the findings of this study are available on request from the corresponding author. The data are not publicly available due to privacy or ethical restrictions.

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