71610-00-9Relevant articles and documents
Microbial hydrolysis of 7-xylosyl-10-deacetyltaxol to 10-deacetyltaxol
Wang, Kang,Wang, Tingting,Li, Jianhua,Zou, Jianhua,Chen, Yongqin,Dai, Jungui
body text, p. 250 - 255 (2011/10/12)
Enterobacter sp. CGMCC 2487, a bacterial strain isolated from the soil around a Taxus cuspidata Sieb. et Zucc. plant, was able to remove the xylosyl group from 7-xylosyltaxanes. The xylosidase of this strain was an inducible enzyme. In the bioconversion of 7-xylosyl-10-deacetyltaxol (7-XDT) to 10-deacetyltaxol (10-DT), for the purpose of enhancing the conversion efficiency, the effects of NH4+, oat xylan, temperature, pH value, cell density and substrate concentration on the bioconversion have been systematically investigated. 3.0 mM NH4+, 0.6% oat xylan in the media could enhance the yield of 10-DT; the optimum biocatalytic temperature was 26 °C and optimum pH value was 6.0. The highest conversion rate and yield of 10-DT from 7-XDT reached 92% and 764 mg/L, respectively. In addition, the biocatalytic capacity of the cell cultures remained 66.1% after continuous three batches. These results indicate that converting 7-XDT to 10-DT, a useful intermediate for the semisynthesis of paclitaxel or other taxane-based anticancer drugs by a novel bacterial strain, Enterobacter sp. CGMCC 2487, would be an alternative for the practical application in the future.
Structure-activity relationship study at the 3'-N-position of paclitaxel: synthesis and biological evaluation of 3'-N-acyl-paclitaxel analogues.
Roh, Eun Joo,Kim, Deukjoon,Lee, Chong Ock,Choi, Sang Un,Song, Choong Eui
, p. 3145 - 3151 (2007/10/03)
A series of 3'-N-acyl-paclitaxel analogues 1a-v were synthesized and their cytotoxicities in vitro against several human tumor cell lines examined. It has been shown that distinct correlation between activity and N-acyl-substituent. The appropriate size of N-acyl group was indispensable for cytotoxicity, and moreover, the presence of beta-substituted conjugated double and triple bond to N-carbonyl generally resulted in increase of cytotoxicities.
A process for the production of taxol
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, (2008/06/13)
A process has been developed for production of taxols A,B,C with high yields from 7-xylosyl-10-deacetyl taxol A (taxol analogue A or, xyloside A), 7-xylosyl-10-deacetyl-taxol B (taxol analogue B or xyloside B), 7-xylosyl-10-deacetyl-taxol C (taxol analogue C or xyloside C), which preferably comprises (i) isolating the taxol analogues A,B,C from the stembark of Taxus wallichianaby an improved process devoid of a solvent partitioning step, (ii) treating the isolated taxol analogues A,B,C with periodates in an acid free polar solvent medium to cleave the diol into dialdehyde at ambient temperature (iii) reducing the dialdehyde solution with borohydride in a polar solvent-acetic acid medium at 0-40°C into an acetal, (iv) acidifying the resultant acetal with a mixture of mineral acid-polar solvent at 0-40°C into intermediate product 10-deacetyl taxols A,B,C (v) reacting 10-deacetyl taxols A or B or C with a silane in presence of a base at 20-40°C to protect 2', 7-hydroxyl groups, of 10-deacetyl taxols A,B,C (vi) acetylating the 10-hydroxyl group in situwith an acetylating agent at 10-40°C, (vii) deprotecting the 2', 7-hydroxyl groups with a mixture of mineral acid-polar solvent at 0-10°C (viii) isolating taxols A or B or C by chromatography over silica.