[Industrial preparative chromatography purification of 10-deacetylpaclitaxel, the enzymatic product of 7-xylosyl-10-deacetylpaclitaxel].
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.
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
Xingbao
X
Liu
Hongwei
H
Luan
Guangbo
G
Ge
Kun
K
Hou
Xunfu
X
Du
Ling
L
Yang
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D043823:Taxoids / Q000138:chemical synthesis* / Q000302:isolation & purification*
C531111:7-xylosyl-10-deacetylpaclitaxel; D043823:Taxoids; C095360:10-deacetylpaclitaxel; D017239:Paclitaxel