Arigoni D, Sagner S, Latzel C, Eisenreich W, Bacher A, Zenk M H
Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule, Universitätsstrasse 16, CH-8092 Zürich, Switzerland.
Proc Natl Acad Sci U S A. 1997 Sep 30;94(20):10600-5. doi: 10.1073/pnas.94.20.10600.
The incorporation of [1-13C]- and [2,3,4,5-13C4]1-deoxy-D-xylulose into beta-carotene, lutein, phytol, and sitosterol in a cell culture of Catharanthus roseus was analyzed by NMR spectroscopy. The labeling patterns of the isoprene precursors, isopentenyl pyrophosphate and dimethylallyl pyrophosphate, were obtained from the terpenes by a retrobiosynthetic approach. 13C Enrichment and 13C13C coupling patterns showed conclusively that 1-deoxy-D-xylulose and not mevalonate is the predominant isoprenoid precursor of phytol, beta-carotene, and lutein. Label from 1-deoxyxylulose was also diverted to phytosterols to a minor extent (6% relative to carotene and phytol formation). The data demonstrate that the formation of isopentenyl pyrophosphate from pentulose occurs strictly by an intramolecular rearrangement process.
采用核磁共振波谱法分析了[1-¹³C]-和[2,3,4,5-¹³C₄]1-脱氧-D-木酮糖掺入长春花细胞培养物中的β-胡萝卜素、叶黄素、叶绿醇和植物甾醇的情况。通过逆生物合成方法从萜类化合物中获得了异戊二烯前体异戊烯基焦磷酸和二甲基烯丙基焦磷酸的标记模式。¹³C富集和¹³C-¹³C偶合模式确凿地表明，1-脱氧-D-木酮糖而非甲羟戊酸是叶绿醇、β-胡萝卜素和叶黄素的主要类异戊二烯前体。来自1-脱氧木酮糖的标记也有少量（相对于胡萝卜素和叶绿醇的形成，为6%）转向植物甾醇。数据表明，由戊酮糖形成异戊烯基焦磷酸严格通过分子内重排过程进行。
