Chinese Journal of Chromatography ›› 2012, Vol. 30 ›› Issue (02): 165-169.DOI: 10.3724/SP.J.1123.2011.10021

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Industrial preparative chromatography purification of 10-deacetylpaclitaxel, the enzymatic product of 7-xylosyl-10-deacetylpaclitaxel

LIU Xingbao, LUAN Hongwei, GE Guangbo, HOU Kun, DU Xunfu, YANG Ling*   

  1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
  • Received:2011-10-20 Revised:2011-12-04 Online:2012-02-28 Published:2012-03-22

Abstract: A scheme for industrial preparative chromatography purification of 10-deacetylpaclitaxel (10-DAP), the semi-synthesized precursor of anticancer drug paclitaxel was developed. 7-Xylosyl-10-deacetylpaclitaxel (10-DAXP) is the most abundant constitute in the needles of Taxus Chinensis, a specific yew species distributed in China. 10-DAXP has been recognized as a good material to convert into 10-DAP, the most ideal precursor of paclitaxel. The partially purified extract from yew needles which mainly contains 10-DAXP (>60%) and other two minor 7-xylosyl-10-deacetyltaxanes including 7-xylosyl-10-deacetylcephalomannine (10-DAXC) and 7-xylosyl-10-deacetylpaclitaxel C (10-DAXP C), was used as the starting material. The total scheme can be divided into four steps. Firstly, the starting material was hydrolyzed by β-xylosidase to remove the C-7 xylosyl group completely; and then the hydrolyzed products mainly containing 10-DAP were eluted on a column packed with resin to get crude 10-DAP (with the purity of 20.5%) with high yield (96.3%). The crude 10-DAP was purified by a column packed with normal phase, and then by a reversed-phase preparative chromatography with ODS as the solid phase. After these two steps, the purity of the aim product 10-DAP was 96% with the overall yield of 79.7%. This novel scheme was suitable for large-scale purification of 10-DAP from 10-DAXP.

Key words: 7-xylosyl-10-deacetylpaclitaxel, 7-xylosyl-10-deacetyltaxane, isolation and purification, paclitaxel, 10-deacetylpaclitaxel, preparative chromatography