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A Family of Related Fungal and Bacterial Di‐ and Sesterterpenes: Studies on Fusaterpenol and Variediene
Author(s) -
Rinkel Jan,
Steiner Simon T.,
Bian Guangkai,
Chen Rong,
Liu Tiangang,
Dickschat Jeroen S.
Publication year - 2020
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201900462
Subject(s) - prenyltransferase , stereochemistry , terpene , absolute configuration , chemistry , enantioselective synthesis , bifunctional , lanostane , enzyme , biosynthesis , biochemistry , catalysis , triterpene , medicine , alternative medicine , pathology
The absolute configuration of fusaterpenol (GJ1012E) has been revised by an enantioselective deuteration strategy. A bifunctional enzyme with a terpene synthase and a prenyltransferase domain from Aspergillus brasiliensis was characterised as variediene synthase, and the absolute configuration of its product was elucidated. The uniform absolute configurations of these and structurally related di‐ and sesterterpenes together with a common stereochemical course for the geminal methyl groups of GGPP unravel a similar conformational fold of the substrate in the active sites of the terpene synthases. For variediene, a thermal reaction observed during GC/MS analysis was studied in detail for which a surprising mechanism was uncovered.