Focused Genome Mining of Structurally Related Sesterterpenes: Enzymatic Formation of Enantiomeric and Diastereomeric Products

Heterologous expression of four clade-A bifunctional terpene synthases (BFTSs), giving di/sesterterpenes with unique polycyclic carbon skeletons such as sesterfisherol, enabled the isolation of the sesterterpenes Bm1, Bm2, Bm3, and Pb1. Their structures suggested that formation of the products occur...

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Veröffentlicht in:	Organic letters 2017-12, Vol.19 (24), p.6696-6699
Hauptverfasser:	Narita, Koji, Sato, Hajime, Minami, Atsushi, Kudo, Kosei, Gao, Lei, Liu, Chengwei, Ozaki, Taro, Kodama, Motoichiro, Lei, Xiaoguang, Taniguchi, Tohru, Monde, Kenji, Yamazaki, Mami, Uchiyama, Masanobu, Oikawa, Hideaki
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkyl and Aryl Transferases - genetics Alkyl and Aryl Transferases - metabolism Aspergillus oryzae - genetics Aspergillus oryzae - metabolism Cyclization Escherichia coli - genetics Escherichia coli - metabolism Genome, Fungal Sesterterpenes - metabolism Stereoisomerism
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Zusammenfassung:	Heterologous expression of four clade-A bifunctional terpene synthases (BFTSs), giving di/sesterterpenes with unique polycyclic carbon skeletons such as sesterfisherol, enabled the isolation of the sesterterpenes Bm1, Bm2, Bm3, and Pb1. Their structures suggested that formation of the products occurs via various diastereomeric carbocation intermediates, allowing the proposal that clade-A BFTSs catalyze three-step cyclizations using several stereofacial combinations of allylic cation–olefin pairs in the corresponding intermediates to generate various stereoisomers.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/acs.orglett.7b03418