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Updated: Oct 31, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Argicyclamides A-C Unveil Enzymatic Basis for Guanidine Bis-prenylation
Chin-Soon Phan, Kenichi Matsuda1,2, Nandani Balloo
1Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Abstract:
Guanidine prenylation is an outstanding modification in alkaloid and peptide biosynthesis, but its enzymatic basis has remained elusive. We report the isolation of argicyclamides, a new class of cyanobactins with unique mono- and bis-prenylations on guanidine moieties, from Microcystis aeruginosa NIES-88. The genetic basis of argicyclamide biosynthesis was established by the heterologous expression and in vitro characterization of biosynthetic enzymes including AgcF, a new guanidine prenyltransferase. This study provides important insight into the biosynthesis of prenylated guanidines and offers a new toolkit for peptide modification.
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