ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
2 files

Epimerization-free C-term Activation of Peptide Fragments by Ball-Milling

preprint
submitted on 01.07.2020 and posted on 02.07.2020 by Yves Yeboue, Marion Jean, Gilles Subra, Jean Martinez, Frédéric Lamaty, Thomas-Xavier Métro
Ball-milling enabled to perform [2+1], [2+2], and [2+3] peptide couplings with high yields and, if any, very low epimerization. Very good results were obtained with peptide fragments containing highly epimerization-prone and/or highly hindered amino acids at C-term such as phenylglycine, cysteine and valine. Ball-milling was clearly identified as the key element to obtain both high yield and purity along with low epimerization. Indeed, the ball-milling conditions proved to be superior to the classical solution synthesis approach on a various array of widely used coupling agents. These results open avenues for the development of highly efficient, convergent and flexible peptide synthesis strategies based on peptide fragment couplings mediated by ball-milling.

Funding

LabEx CheMISyst through ANR programme ANR-10-LABX-05-01

History

Email Address of Submitting Author

thomas-xavier.metro@umontpellier.fr

Institution

CNRS

Country

France

ORCID For Submitting Author

0000-0003-2280-3595

Declaration of Conflict of Interest

No conflict of interest to declare.

Exports