Open AccessBiosynthesis of para-Cyclophane-Containing Hirsutellone Family of Fungal Natural Products
Author(s) -
M. Ohashi,
Thomas B. Kakule,
Man-Cheng Tang,
Cooper S. Jamieson,
Mengting Liu,
YiLei Zhao,
K. N. Houk,
Yi Tang
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.1c00098
Subject(s) - cyclophane , chemistry , stereochemistry , ring (chemistry) , oxidoreductase , cycloaddition , crystal structure , biochemistry , crystallography , organic chemistry , enzyme , catalysis
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 A 2 ( 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.