Biosynthesis of taxol: enzymatic acetylation of 10-deacetylbaccatin-III to baccatin-III in crude extracts from roots of Taxus baccata

Biochemical and Biophysical Research Communications
R ZocherD Ewald

Abstract

The biosynthesis of taxol is a multistep process. One intermediate reaction is the acetylation of 10-deacetylbaccatin-III (10-DAB) to baccatin-III, an assumed precursor of taxol. Here we describe the cell free acetylation of 10-DAB in crude extracts from roots of Taxus baccata saplings using 14C-or 3H-labeled acetyl-coenzyme A as the acetyl donor. The reaction is strictly dependent on the addition of 10-DAB and is specific for the 10-hydroxyl group of the taxane ring. Formation of radiolabeled baccatin-III was confirmed by co-chromatography of the labeled product with authentic baccatin-III in different TLC-systems and HPLC. Furthermore, the acetylation product showed an identical UV spectrum as authentic baccatin-III. Crude extracts from cambium of stems yielded three- to fivefold lower activity. This is in agreement with our finding that the taxol titer in roots was considerably higher than that in cambium.

Citations

Jan 19, 2000·Proceedings of the National Academy of Sciences of the United States of America·K Walker, R Croteau
Feb 1, 2006·Phytochemistry Reviews : Proceedings of the Phytochemical Society of Europe·Rodney CroteauMark R Wildung
Nov 25, 2006·Applied Microbiology and Biotechnology·Dieter Frense
Apr 20, 2001·Bioorganic & Medicinal Chemistry·D A SunL O Zamir
Aug 16, 2001·Bioorganic & Medicinal Chemistry·D A SunL O Zamir
Nov 2, 1999·Journal of Natural Products·E Baloglu, D G Kingston

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