Greener cleavage of protected peptide fragments from Sieber Amide Resin.
Author(s)
Al Musaimi, Othman
Gavva, Varshitha
Williams, Daryl R
Type
Journal Article
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.
Date Issued
2023-01-23
Date Acceptance
2022-12-20
Citation
ChemistryOpen, 2023, 11 (12), pp.1-7
ISSN
2191-1363
Publisher
Wiley
Start Page
1
End Page
7
Journal / Book Title
ChemistryOpen
Volume
11
Issue
12
Copyright Statement
© 2022 The Authors. Published by Wiley-VCH GmbH
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
License URL
Identifier
https://www.ncbi.nlm.nih.gov/pubmed/36564351
Subjects
Sieber amide resin
fragments condensation
green chemistry
peptide cleavage
protected peptide amide
Peptide Fragments
Amides
Methylene Chloride
Peptides
Amino Acids
Resins, Plant
Publication Status
Published
Coverage Spatial
Germany
Date Publish Online
2022-12-23