Studies on the biosynthesis of taxol: the taxane carbon skeleton is not of mevalonoid origin.

• DOI: 10.1073/pnas.93.13.6431
• Publication Date: 2002-07-26T14:34:16Z
• Authors: W Eisenreich; B Menhard; P J Hylands; M H Zenk; A Bacher
• Keywords: Taxoid; Taxane; Terpene; Moiety

A cell culture of Taxus chinensis was established to produce the diterpene 2alpha,5alpha,10beta,14beta-tetra-acetoxy4 ++ +(20),11-taxadiene (taxuyunnanine C) in 2.6% (dry weight) yield. The incorporation [U-13C6]glucose, [1-13C]glucose, and [1,2-13C2]acetate into this analyzed by NMR spectroscopy. Label from diverted four acetyl groups taxuyunnanine C, but not taxane ring system. [1-13C]glucose [U-13C6]glucose efficiently incorporated both system groups. isoprenoid moieties showed identical labeling patterns. analysis long-range 13C13C couplings C obtained an experiment with documents involvement intramolecular rearrangement biosynthesis precursor. patterns are inconsistent mevalonate pathway. taxoid data share important features alternative pathway operating certain eubacteria Rohmer, M., Knani, Simonin, P., Sutter, B. & Sahm, H. (1993) Biochem. J. 295, 517-524].