Heterologous expression of a single fungal HR-PKS leads to the formation of diverse 2-alkenyl-tetrahydropyrans in model fungi. Issue 38 (16th September 2021)

• Record Type: Journal Article
• Authors: Lyu, Hai-Ning; Zhang, Jinyu; Zhou, Shuang; Liu, Hong-Wei; Zhuang, Wen-Ying; Li, Shu-Ming; Yin, Wen-Bing
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 38(2021)
• Page Start: 8377
• Page End: 8383
• Publication Date: 2021-09-16
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01501j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : We present the first example that a single fungal HR-PKS could synthesize multiple complicated compounds. Abstract : 2-Alkenyl-tetrahydropyrans belong to a rare class of natural products that exhibit broad antifungal activities. Their structural instability and rareness in nature have restrained their discovery and drug development. In this study, the heterologous expression of a single highly reducing polyketide synthase (HR-PKS, App1) from Trichoderma applanatum in Aspergillus nidulans leads to the formation of seven 2-alkenyl-tetrahydropyran derivatives including one known compound virensol C (1 ) and six new compounds (2–7 ). However, introducing App1 into Saccharomyces cerevisiae resulted in the identification of additional two 2-alkenyl-tetrahydropyrans lacking the hydroxyl or methoxyl group at the C-2 position (8 and 9 ). The structures of the isolated compounds were elucidated by extensive spectroscopic analysis using NMR and HR-ESI-MS.