Related Experiment Video
Updated: May 19, 2026

Targeting Cysteine Thiols for in Vitro Site-specific Glycosylation of Recombinant Proteins
Published on: October 4, 2017
Armed-disarmed effect on the stability of cysteine thioglucosides
Mbulelo G Nokwequ1, Comfort M Nkambule, David W Gammon
1Department of Chemistry, Tshwane University of Technology, Pretoria 0001, South Africa. nokwequmg@tut.ac.za
Abstract:
Thioglucosides of cysteine show variable stability depending on the nature of the protecting groups on the glycosyl donor. Armed protecting groups (benzyl) lead to products that decompose readily while disarmed protecting groups (acetyl) lead to more stable products. Since this armed/disarmed effect of the protecting group on the stability of the thioglucosides is more pronounced for cysteine with an unprotected carboxylic group, the proposed mechanism is that decomposition is initiated by an intramolecular protonation of glycosyl sulfide and subsequent displacement of the sulfide by adventitious nucleophiles.
More Related Videos
Related Concept Videos
Inhibitors of Bacterial Protein Synthesis
Substituent Effects on Acidity of Carboxylic Acids
Complexation Equilibria: The Chelate Effect
Factors Affecting Dissolution: Drug Permeability, Stability and Stereochemistry
Complexation Equilibria: Factors Influencing Stability of Complexes
Skeletal Muscle Relaxants: Adverse Effects
Unlike...

