Related Experiment Video
Updated: Jun 12, 2026

Profiling Ubiquitin and Ubiquitin-like Dependent Post-translational Modifications and Identification of Significant Alterations
Published on: November 7, 2019
Protecting group variations of delta-mercaptolysine useful in chemical ubiquitylation
Mahmood Haj-Yahya1, K S Ajish Kumar, Lesly A Erlich
1Department of Chemistry, Ben-Gurion University of the Negev, Beer Sheva 84105, Israel.
Abstract:
The high efficiency and chemoselectivity of peptide ubiquitylation that is achieved using the delta-mercaptolysine prompted us to expand the scope of this residue in various ligation schemes. In this report, we demonstrate the synthesis of five analogues of this important amino acid bearing a variety of protecting groups, which is essential in sequential peptide ligation and ubiquitylation. The key-step in the synthesis is the nucleophilic 1,4-addition of a variety of thiols on a nitro olefin scaffold.
Related Concept Videos
Covalently Linked Protein Regulators
These groups modify specific amino acids in a protein.
Protecting Groups for Aldehydes and Ketones: Introduction
Protection of Alcohols
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...

