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首页> 外文期刊>Proceedings of the National Academy of Sciences of the United States of America >Dimethylallyl pyrophosphate is not the committed precursor of isopentenyl pyrophosphate during terpenoid biospothesis from 1-deoxyxylulose in higher plants
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Dimethylallyl pyrophosphate is not the committed precursor of isopentenyl pyrophosphate during terpenoid biospothesis from 1-deoxyxylulose in higher plants

机译：在高等植物中从1-脱氧木酮糖类萜类生物合成过程中，二甲基烯丙基焦磷酸不是异戊烯基焦磷酸的固定前体

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摘要

Cell cultures of Catharanthus roseus were supplied with [2-13,C,3-2H]-deoxyxylulose or [2-`13C,4-2H]1- deoxyxylulose. Lutein and chlorophylls were isolated from the cell mass, and hydrolysis of the chlorophyll mixtures afforded phytol. Isotope labeling patterns of phytol and lutein were determincd by 2H NMR and 1H,2H-decoupled 13C NMR. From the data it must be concluded that the deuterium atom in position 3 of deoxyxylulose was incorporated into both iso- pentenyl pyrophosphate (IPP) and dimethylallyl pyrophos- phate with a rate of 75 (with respect to the internal 13C label). The detected stereochcmical signature implies that the Iabel is located preferentially in the (E)-hydrogen atom of IPP. This preferential labeling, in turn, rules out dimethylallyl pyrophosphate as the compulsory precursor of IPP. In the expcriment with [2-13C,4-2R]l-deoxyxylulose, the 13C label was efFicicntly transferred to the terpenoids whereas the 2H Iabel was completely washed out, most probably after IPP formation as a consequence or the isomerization and elonga- tion process. In addition, the data cast light on the stereo- chemical course of the dehydrogenation and cyclization steps involved in the biosynthesis of lutdin.
机译：向长春花的细胞培养物提供[2-13，C，3-2H]-脱氧木果糖或[2-`13C，4-2H] 1-脱氧木果糖。从细胞团中分离出叶黄素和叶绿素，并水解叶绿素混合物得到植醇。植醇和叶黄素的同位素标记模式由2H NMR和1H，2H解耦的13C NMR确定。从数据必须得出的结论是，脱氧木酮糖第3位的氘原子以75的比率（相对于内部13C标记）掺入了焦磷酸异戊烯基酯和焦磷酸二甲基烯丙基酯中。检测到的立体化学特征暗示Iabel优先位于IPP的（E）-氢原子中。反过来，这种优先标记排除了焦磷酸二甲基烯丙酯作为IPP的强制性前体。在使用[2-13C，4-2R] 1-脱氧木酮糖的实验中，有效地将13C标记转移到了萜类化合物上，而2H Iabel被完全洗掉了，很可能是在IPP形成后或异构化和延伸后处理。此外，数据还揭示了卢迪丁生物合成中涉及的脱氢和环化步骤的立体化学过程。

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