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Updated: May 27, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Pericyclic prenylation: peptide modification through a Claisen rearrangement
Jaimeen D Majmudar1, Richard A Gibbs
1Department of Medicinal Chemistry and Molecular Pharmacology, The Purdue University Center for Cancer Research, West Lafayette, IN 47906, USA.
Abstract:
LynF prenylates, but the prenyl migrates: Schmidt and co-workers have demonstrated that LynF from Lyngbya aestuarii is a reverse O-prenyl transferase. However, a forward C-prenylated product is obtained through a non-enzymatic Claisen rearrangement. The elucidation of this unprecedented two-step process is a significant contribution to our understanding of the biosynthesis of complex macrocyclic peptides.
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