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

• Published in: Sepu Vol. 30; no. 2; p. 165
• Main Authors: Liu, Xingbao, Luan, Hongwei, Ge, Guangbo, Hou, Kun, Du, Xunfu, Yang, Ling
• Format: Journal Article
• Language: Chinese
• Published: China 01.02.2012
• Subjects: Chromatography, High Pressure Liquid - methods; Paclitaxel - analogs & derivatives; Paclitaxel - chemistry; Paclitaxel - metabolism; Taxoids - chemical synthesis; Taxoids - isolation & purification
• ISSN: 1000-8713
• DOI: 10.3724/SP.J.1123.2011.10021

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 beta-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.