Regioselectivity of taxoid-O-acetyltransferases: heterologous expression and characterization of a new taxadien-5alpha-ol-O-acetyltransferase

Archives of Biochemistry and Biophysics
MyDoanh ChauRodney B Croteau

Abstract

In addition to the anticancer drug Taxol, yew (Taxus) species produce a large variety of other taxane diterpenoids which differ mainly in the type of acyl and aroyl groups appended to the many hydroxyl functions on the taxane core; acetate esters are particularly common. Taxol bears an acetate at C10 and another at C4 thought to originate by intramolecular migration of a C5 acetate function in the process of oxetane ring formation, but many other naturally occurring taxoids bear acetate groups at C1, C2, C7, C9, and C13, in addition to C5 and C10. cDNAs encoding a taxoid 5alpha-O-acetyltransferase (taxadien-5alpha-ol as substrate) and a taxoid 10beta-O-acetyltransferase (10-deacetylbaccatin III as substrate) have been acquired from a recently isolated family of Taxus acyl/aroyltransferase clones. To explore the origins of other acetylated taxoids, the group of recombinant Taxus acyltransferases was investigated with a range of polyhydroxylated taxoids as substrates. From this survey, a new acetyltransferase clone (denoted TAX19) was identified that was capable of acetylating taxadien-5alpha-ol with activity comparable to that of the previously identified 5alpha-O-acetyltransferase (clone TAX1). However, when these two recombina...Continue Reading

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Citations

Nov 25, 2006·Applied Microbiology and Biotechnology·Dieter Frense
Apr 30, 2005·Current Opinion in Plant Biology·Kirsten JørgensenBirger Lindberg Møller
Feb 1, 2006·Phytochemistry Reviews : Proceedings of the Phytochemical Society of Europe·Rodney CroteauMark R Wildung
Dec 1, 2018·The Journal of Biological Chemistry·Sean R JohnsonBjörn Hamberger
Sep 15, 2005·Biotechnology and Bioengineering·JingHong M DejongRodney B Croteau
May 26, 2018·Applied Biochemistry and Biotechnology·Lin-Feng YouJia-Jun Huang
Jul 10, 2020·DNA Research : an International Journal for Rapid Publication of Reports on Genes and Genomes·Kin H LauC Robin Buell
Feb 9, 2019·Phytochemistry·Ulschan Bathe, Alain Tissier
Nov 15, 2008·Journal of the American Chemical Society·Mark E Ondari, Kevin D Walker
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tao WangZhong Wang
Jul 31, 2021·Phytochemistry·B Markus Lange, Caleb F Conner

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