Related Experiment Video
Updated: May 30, 2026

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
Published on: November 2, 2016
Solid supported chemical syntheses of both components of the lantibiotic lacticin 3147
Wei Liu1, Alice S H Chan, Hongqiang Liu
1Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
Abstract:
Lantibiotics are antimicrobial peptides produced by bacteria. Some are employed for food preservation, whereas others have therapeutic potential due to their activity against organisms resistant to current antibiotics. They are ribosomally synthesized and posttranslationally modified by dehydration of serine and threonine residues followed by attack of thiols of cysteines to form monosulfide lanthionine and methyllanthionine rings, respectively. Chemical synthesis of peptide analogues is a powerful method to verify stereochemistry and access structure-activity relationships. However, solid supported synthesis of lantibiotics has been difficult due to problems in generating lanthionines and methyllanthionines with orthogonal protection and good stereochemical control. We report the solid-phase syntheses of both peptides of a two-component lantibiotic, lacticin 3147. Both successive and interlocking ring systems were synthesized on-resin, thereby providing a general methodology for this family of natural products.
Related Concept Videos
Production of Antibiotics
Production of Organic Acids
Production of Pharmaceuticals
Formation of Lipopolysaccharides
Inhibitors of Gram-positive Cell Wall Synthesis
