Related Experiment Video
Updated: Apr 3, 2026

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides
Published on: August 20, 2018
Thiazolidine-Protected β-Thiol Asparagine: Applications in One-Pot Ligation-Desulfurization Chemistry
Jessica Sayers1, Robert E Thompson1, Kristen J Perry1
1School of Chemistry, The University of Sydney , Sydney, New South Wales 2006, Australia.
Abstract:
The synthesis of a β-thiol asparagine derivative bearing a novel (2,4,6-trimethoxyphenyl)thiazolidine protecting group is described. The efficient incorporation of the amino acid into the N-termini of peptides is demonstrated as well as the utility of the β-thiol asparagine moiety for rapid ligation reactions with peptide thioesters. The streamlined synthesis of native peptide products could be accomplished using a one-pot radical desulfurization of the β-thiol auxiliary following the ligation event. The utility of the amino acid is highlighted in the efficient one-pot assembly of the HIV entry inhibitor enfuvirtide.
More Related Videos
Related Concept Videos
Preparation and Reactions of Thiols
Preparation and Reactions of Sulfides
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Sulfur Assimilation
Diazonium Group Substitution: –OH and –H

