Formation of Terrestric Acid in Penicillium crustosum Requires Redox-Assisted Decarboxylation and Stereoisomerization.,Organic Letters

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Formation of Terrestric Acid in Penicillium crustosum Requires Redox-Assisted Decarboxylation and Stereoisomerization.
Organic Letters ( IF 4.9 ) Pub Date : 2019-12-13 , DOI: 10.1021/acs.orglett.9b04002
Jie Fan ₁ , Ge Liao ₁ , Lena Ludwig-Radtke ₁ , Wen-Bing Yin ₂ , Shu-Ming Li ₁

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Crustosic acid (1) differs from terrestric acid (2) by a 5β-carboxylmethyl at the tetronate ring instead of a 5α-methyl group in Penicillium crustosum. The formation of 1 via carboxylcrustic and viridicatic acid was confirmed by gene deletion and heterologous expression. The conversion of 1 to 2 requires a decarboxylation-mediated olefination by TraH and subsequent reduction by TraD. The redox-assisted decarboxylation and stereoisomerization proved the biosynthetic relationships of fungal acyltetronates with different stereochemistry.

中文翻译：

在青霉菌中形成terrestric酸需要氧化还原辅助的脱羧和立体异构化。

硬脂酸（1）与陆地酸（2）的不同之处在于，在青蒿环的环上有5β-羧甲基，而不是5α-甲基。通过基因缺失和异源表达证实了经由羧壳酸和吡啶二酸形成的1。1到2的转化需要通过TraH进行脱羧介导的烯化反应，然后通过TraD进行还原。氧化还原辅助的脱羧和立体异构化证明了具有不同立体化学性质的真菌酰基四酸酯的生物合成关系。

更新日期：2019-12-17

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