Biosynthesis of <i>para-</i>Cyclophane-Containing Hirsutellone Family of Fungal Natural Products
Masao Ōhashi, Thomas B. Kakule, Man‐Cheng Tang, Cooper S. Jamieson, Mengting Liu, Yi‐Lei Zhao, K. N. Houk, Yi Tang
Abstract
Hirsutellones are fungal natural products containing a macrocyclic para-cyclophane connected to a decahydrofluorene ring system. We have elucidated the biosynthetic pathway for pyrrocidine B (3) and GKK1032 A2 (4). Two small hypothetical proteins, an oxidoreductase and a lipocalin-like protein, function cooperatively in the oxidative cyclization of the cyclophane, while an additional hypothetical protein in the pyrrocidine pathway catalyzes the exo-specific cycloaddition to form the cis-fused decahydrofluorene.
Topics & Concepts
ChemistryCyclophaneStereochemistryCycloadditionRing (chemistry)OxidoreductaseCrystal structureBiochemistryCrystallographyOrganic chemistryEnzymeCatalysisPlant biochemistry and biosynthesisMicrobial Natural Products and BiosynthesisPhotosynthetic Processes and Mechanisms