Identification of Intermediates in the Biosynthesis of PR Toxin by Penicillium roqueforti
Identification of Intermediates in the Biosynthesis of PR Toxin by Penicillium roqueforti
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DOI：
10.1002/anie.201506128
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发表时间：
2015-10-05
影响因子：
16.6
通讯作者：
Dickschat, Jeroen S.
中科院分区：
文献类型：
--
作者：
Riclea, Ramona;Dickschat, Jeroen S.
倍半萜类化合物7-epi-neopetasone是通过Wieland-Miescher酮合成的。该化合物与先前暂时鉴定的罗克弗青霉顶空成分相同。用C-13-标记的甲羟戊酸内酯同位素异构体的进料实验表明，在C12处的氧化和C11=C12到C7=C11双键的异构化必须独立地发生，而不是通过C7-C11-C12烯丙基在一个步骤中发生。喂食（11，12，13-C-13（3））-7-epi-neopetasone导致PR毒素的标记，从而确定该化合物为新鉴定的途径中间体。
The sesquiterpenoid 7-epi-neopetasone was synthesized via the Wieland-Miescher ketone. The compound was identical to a previously tentatively identified headspace constituent of Penicillium roqueforti. Feeding experiments with C-13-labeled mevalonolactone isotopomers demonstrated that oxidation at C12 and an isomerization of the C11=C12 to a C7=C11 double bond must occur independently and not via a C7-C11-C12 allyl radical in one step. Feeding with (11,12,13-C-13(3))-7-epi-neopetasone resulted in labelling of the PR toxin, thus establishing this compound as a newly identified pathway intermediate.