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

07 August 2020, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

NCL
ligation
thioester
solid-phase synthesis
peptide
chemical protein synthesis
native chemical ligation
epimerization
reductive amination

Supplementary materials

Title
Description
Actions
Title
OpitmisationHnb-SI
Description
Actions

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