Terpenoid biosynthesis from 1-deoxy-D-xylulose in higher plants by intramolecular skeletal rearrangement.
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.
Arigoni
D
D
Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule, Universitätsstrasse 16, CH-8092 Zürich, Switzerland.
Sagner
S
S
Latzel
C
C
Eisenreich
W
W
Bacher
A
A
Zenk
M H
MH
D002478:Cells, Cultured; D009682:Magnetic Resonance Spectroscopy; D059828:Plant Cells; D010944:Plants / Q000378:metabolism*; D013729:Terpenes / Q000737:chemistry / Q000378:metabolism*; D014996:Xylulose / Q000031:analogs & derivatives* / Q000378:metabolism
D013729:Terpenes; D014996:Xylulose; C029724:1-deoxy-2-pentulose