Discovery and Elucidation of the Biosynthesis of Aspernidgulenes: Novel Polyenes from Aspergillus Nidulans by Using Serial Promoter Replacement

doi:10.1002/cbic.201800486

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標題:	Discovery and Elucidation of the Biosynthesis of Aspernidgulenes: Novel Polyenes from Aspergillus Nidulans by Using Serial Promoter Replacement
作者:	Lin, Tzu-Shyang Chen, Bethany Chiang, Yi-Ming Wang, Clay C. C.
貢獻者:	Univ Southern Calif, Sch Pharm, Dept Pharmacol & Pharmaceut Sci Chia Nan Univ Pharm & Sci, Dept Pharm Univ Southern Calif, Coll Letters Arts & Sci, Dept Chem
關鍵字:	aspernidgulenes biosynthesis natural products polyenes polyketides
日期:	2019-02
上傳時間:	2020-07-29 13:48:05 (UTC+8)
出版者:	WILEY-V C H VERLAG GMBH
摘要:	Through serial promoter exchanges, we isolated several novel polyenes, the aspernidgulenes, from Aspergillus nidulans and uncovered their succinct biosynthetic pathway involving only four enzymes. An enoyl reductase (ER)-less highly reducing polyketide synthase (HR-PKS) putatively produces a 5,6-dihydro-alpha-pyrone polyene, which undergoes bisepoxidation, epoxide ring opening, cyclization, and hydrolytic cleavage by three tailoring enzymes to generate aspernidgulene A1 and A2. Our findings demonstrate the prowess of fungal-tailoring enzymes to transform a polyketide scaffold concisely and efficiently into complex structures. Moreover, comparison with citreoviridin and aurovertin biosynthesis suggests that methylation of the alpha-pyrone hydroxy group by methyltransferase (CtvB or AurB) is the branching point at which the biosynthesis of these two classes of compounds diverge. Therefore, scanning for the presence or absence of the gatekeeping alpha-pyrone methyltransferase gene in homologous clusters might be a potential way to classify the product bioinformatically as belonging to methylated alpha-pyrone polyenes or polyenes containing rings derived from the cyclization of the unmethylated 5,6-dihydro-alpha-pyrone, such as 2,3-dimethyl-gamma-lactone and oxabicyclo[2.2.1]heptane.
關聯:	Chembiochem, v.20, n.3, pp.329-334
顯示於類別:	[藥學系(所)] 期刊論文

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