Propylphosphonic anhydride (T3P) as green coupling reagent for solid-phase peptide synthesis
File(s)
Author(s)
Almusaimi, Othman
Albericio, Fernando
de la Torre, Beatriz
Type
Journal Article
Abstract
Amidation is the predominant reaction within the pharmaceutical setting, and it is attracting greater attention due to the increased demand for therapeutic peptides. The high therapeutic efficacy and safety profile of peptides have placed these molecules in prime position within the pharmaceutical arena, which is reflected by these molecules receiving several approvals from various regulatory agencies each year. In this context, the demand for developing efficient strategies for peptide synthesis has also risen. Although propylphosphonic anhydride (T3P®), which has been recently proposed as a green coupling reagent, has shown good performance in solution, it has never been applied to solid‐phase peptide synthesis (SPPS). Here we test the use of T3P® for SPPS. Satisfactory yields were achieved with a mild activation protocol. Various green solvents were tested and proved to be compatible with this coupling reagent. Several commonly used reagents cause allergic reactions or are susceptible to explosion under certain conditions. To overcome these issues, we propose T3P® as a potential alternative coupling reagent in SPPS.
Date Issued
2021-03-19
Date Acceptance
2021-12-20
Citation
ChemistrySelect, 2021, 6 (11), pp.2649-2657
ISSN
2365-6549
Publisher
Wiley
Start Page
2649
End Page
2657
Journal / Book Title
ChemistrySelect
Volume
6
Issue
11
Copyright Statement
© 2021 Wiley‐VCH GmbH. This is the accepted version of the following article: O. Al Musaimi, R. Wisdom, P. Talbiersky, B. G. De La Torre, F. Albericio, ChemistrySelect 2021, 6, 2649, which has been published in final form at https://doi.org/10.1002/slct.202100123
Identifier
https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/slct.202100123
Source
Bonding Through Chemistry, ACS spring 2022
Subjects
03 Chemical Sciences
Publication Status
Published
Start Date
2022-03-20
Coverage Spatial
San Diego, CA
Date Publish Online
2021-02-16