An Unusual Chimeric Diterpene Synthase from Emericella variecolor and Its Functional Conversion into a Sesterterpene Synthase by Domain Swapping. (5th November 2015)

• Record Type: Journal Article
• Authors: Qin, Bin; Matsuda, Yudai; Mori, Takahiro; Okada, Masahiro; Quan, Zhiyang; Mitsuhashi, Takaaki; Wakimoto, Toshiyuki; Abe, Ikuro
• Is Part Of: Angewandte Chemie. Volume 128:Number 5(2016)
• Page Start: 1690
• Page End: 1693
• Publication Date: 2015-11-05
• Subjects: Biosynthese -- Domänenaustausch -- Prenyltransferasen -- Sesterterpenoide -- Terpencyclasen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201509263
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Di‐ and sesterterpene synthases produce C20 and C25 isoprenoid scaffolds from geranylgeranyl pyrophosphate (GGPP) and geranylfarnesyl pyrophosphate (GFPP), respectively. By genome mining of the fungus Emericella variecolor, we identified a multitasking chimeric terpene synthase, EvVS, which has terpene cyclase (TC) and prenyltransferase (PT) domains. Heterologous gene expression in Aspergillus oryzae led to the isolation of variediene (1 ), a novel tricyclic diterpene hydrocarbon. Intriguingly, in vitro reaction with the enzyme afforded the new macrocyclic sesterterpene2 as a minor product from dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). The TC domain thus produces the diterpene1 and the sesterterpene2 from GGPP and GFPP, respectively. Notably, a domain swap of the PT domain of EvVS with that of another chimeric sesterterpene synthase, EvSS, successfully resulted in the production of2 in vivo as well. Cyclization mechanisms for the production of these two compounds are proposed.