An effective method to produce 7-epitaxol from taxol in HCO3

Yanjie Liu; Xiaoyu Ma; Mengkai Zhou; Xiaoran Hao; Xudong Zhu

doi:10.1016/j.bmcl.2020.127285

An effective method to produce 7-epitaxol from taxol in HCO₃

Bioorg Med Chem Lett. 2020 Aug 1;30(15):127285. doi: 10.1016/j.bmcl.2020.127285. Epub 2020 May 26.

Authors

Yanjie Liu¹, Xiaoyu Ma¹, Mengkai Zhou¹, Xiaoran Hao¹, Xudong Zhu²

Affiliations

¹ Beijing Key Laboratory of Genetic Engineering Drug and Biotechnology, Institute of Biochemistry and Biotechnology, College of Life Science, Beijing Normal University, Beijing 100875, PR China.
² Beijing Key Laboratory of Genetic Engineering Drug and Biotechnology, Institute of Biochemistry and Biotechnology, College of Life Science, Beijing Normal University, Beijing 100875, PR China. Electronic address: zhu11187@bnu.edu.cn.

PMID: 32527458
DOI: 10.1016/j.bmcl.2020.127285

Abstract

It is known that 7-epitaxol has much stronger cytotoxicity than taxol does. However, the content of 7-epitaxol in yew is much less than taxol, which makes it more costly to obtain. We describe here a method to effectively convert taxol to 7-epitaxol. The key condition for reaction needs NaHCO₃ in solvent acetonitrile (ACN). The conversion rate can be over 82%.

Keywords: 7-Epitaxol; Acetonitrile; Epimerization; HCO(3)(–); Taxol.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetonitriles / chemistry
Antifungal Agents / chemical synthesis*
Antifungal Agents / chemistry
Antifungal Agents / pharmacology
Microbial Sensitivity Tests
Molecular Conformation
Paclitaxel / analogs & derivatives
Paclitaxel / chemical synthesis*
Paclitaxel / chemistry
Paclitaxel / pharmacology
Saccharomyces cerevisiae / drug effects
Sodium Bicarbonate / chemistry*

Substances

Acetonitriles
Antifungal Agents
Sodium Bicarbonate
Paclitaxel
acetonitrile