• Dr. Allyn T. Londregan (second from left) with his co-workers Kathleen A. Farley, Chris Limberakis and David W. Piotrowski (from left)


Synthesis and Analysis of Macrocyclic Peptides with 310-Helical Structure

Allyn Londregan describes the synthesis and analysis of macrocyclic peptides in SYNLETT.

Synthesis and Analysis of Macrocyclic Peptides with 310-Helical Structure: Allyn T. Londregan and co-workers Synlett 2015, DOI: 10.1055/s-0034-1380507

Conformationally constrained peptides, such as macrocyclic peptides having rigidified secondary structures, are privileged scaffolds in medicinal chemistry and drug discovery. Recently, a group of researchers from Pfizer Inc. (Groton, USA) led by Dr. Allyn T. Londregan reported in SYNLETT a novel and practical protocol for the synthesis of macrocyclic peptides having predominantly 310-helical secondary structures. The protocol relies on a PyBroP-mediated cyclization involving a nucleophilic attack of a free amino residue of a tyrosine, histidine, lysine, ornithine, etc. on the activated 2-position of a pyridine-N-oxide phenylalanine mimic, and is facilitated by solid-phase synthesis.

  • Macrocyclic peptide with 310-helix

Dr. Londregan said: “New techniques to synthesize macrocyclic peptides with defined secondary structures will be useful for the discovery of peptide-based medicines.”
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