Focused Genome Mining of Structurally Related Sesterterpenes: Enzymatic Formation of Enantiomeric and Diastereomeric Products
| Autor: | Kosei Kudo, Masanobu Uchiyama, Hajime Sato, Mami Yamazaki, Motoichiro Kodama, Chengwei Liu, Atsushi Minami, Tohru Taniguchi, Lei Gao, Kenji Monde, Taro Ozaki, Hideaki Oikawa, Koji Narita, Xiaoguang Lei |
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| Rok vydání: | 2017 |
| Předmět: |
Allylic rearrangement
Sesterterpenes Stereochemistry Aspergillus oryzae Stereoisomerism Carbocation 010402 general chemistry 01 natural sciences Biochemistry Terpene chemistry.chemical_compound Escherichia coli Physical and Theoretical Chemistry Bifunctional Alkyl and Aryl Transferases 010405 organic chemistry Chemistry Organic Chemistry Diastereomer Combinatorial chemistry 0104 chemical sciences Cyclization Genome Fungal Enantiomer |
| Zdroj: | Organic Letters. 19:6696-6699 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.7b03418 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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