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These are preliminary reports that have not been peer-reviewed.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
0/0

Reinvestigation of a Critical Reductive Amination Step Leads to an Optimized Protocol for the Synthesis of N-2-Hydroxybenzylcysteine Peptide Crypto-Thioesters

preprint
revised on 22.08.2020 and posted on 24.08.2020 by Skander Abboud, Vincent AUCAGNE
An in-depth study of the Fmoc-based solid phase peptide synthesis of N-Hnb-Cys crypto-thioester peptides, advantageous building blocks for the native chemical ligation-based synthesis of proteins, led to the identification of epimerized and imidazolidinone side products formed during a key reductive amination step. The understanding of the underlying reaction mechanisms was crucial for the developement of an automatable optimized synthetic protocol.

Funding

French national funding agency ANR (EasyMiniprot project, ANR-15-CE07-0022)

History

Email Address of Submitting Author

aucagne@cnrs-orleans.fr

Institution

CNRS - Centre de Biophysique Moléculaire

Country

France

ORCID For Submitting Author

0000-0002-2647-0188

Declaration of Conflict of Interest

No conflict of interest to declare.

Exports