Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis†Electronic supplementary information (ESI) available: Containing all experimental details. See DOI: 10.1039/c3sc52911hClick here for additional data file.
Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis†Electronic supplementary information (ESI) available: Containing all experimental details. See DOI: 10.1039/c3sc52911hClick here for additional data file.
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DOI：
10.1039/c3sc52911h
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发表时间：
2014-02-23
期刊：
影响因子：
8.4
通讯作者：
Cox RJ
中科院分区：
文献类型：
--
作者：
Fahad AA;Abood A;Fisch KM;Osipow A;Davison J;Avramović M;Butts CP;Piel J;Simpson TJ;Cox RJ
基于对二氢山梨西林10 b氧化脱芳反应的观察，提出了一条新的生物合成山梨西林类天然产物的途径。从产黄青霉（Penicillium chrysogenum）E01-10/3中克隆了一个FAD依赖的单加氧酶基因（SorbC），并在大肠杆菌中进行了可溶性表达。该酶能有效地进行山梨西林和二氢山梨西林的氧化脱芳，分别得到山梨西林醇和二氢山梨西林醇。对SorbC周围基因簇的生物信息学检查表明存在两个聚酮合酶（PKS）编码基因，命名为sorbA和sorbB。基因sorbA编码高度还原的迭代PKS，而SorbB编码非还原的迭代PKS，其特征在于通常参与聚酮醛的生产的还原释放结构域。利用这些观察结果和以前报道的结果，从同位素饲养实验一个新的和更简单的生物合成路线索比西林类的次级代谢产物的建议，这是与所有报道的实验结果一致。
A new biosynthetic pathway to the sorbicillinoid natural products is proposed based on the observation of oxidative dearomatisation of dihydrosorbicillin 10b. An FAD-dependent monooxygenase encoding gene (SorbC) was cloned from Penicillium chrysogenum E01-10/3 and expressed as a soluble protein in Escherichia coli. The enzyme efficiently performed the oxidative dearomatisation of sorbicillin and dihydrosorbicillin to give sorbicillinol and dihydrosorbicillinol respectively. Bioinformatic examination of the gene cluster surrounding SorbC indicated the presence of two polyketide synthase (PKS) encoding genes designated sorbA and sorbB. The gene sorbA-encodes a highly reducing iterative PKS while SorbB encodes a non-reducing iterative PKS which features a reductive release domain usually involved in the production of polyketide aldehydes. Using these observations and previously reported results from isotopic feeding experiments a new and simpler biosynthetic route to the sorbicillin class of secondary metabolites is proposed which is consistent with all reported experimental results.
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