10-O-去乙酰基-7-O-beta-D-吡喃木糖基浆果赤霉素 III | 157664-03-4

• 物质功能分类: 天然产物 - 萜类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 10-O-去乙酰基-7-O-beta-D-吡喃木糖基浆果赤霉素 III
• 中文别名: 10-O-去乙酰基-7-O-BETA-D-吡喃木糖基浆果赤霉素III；10-O-去乙酰基-7-O-beta-D-吡喃木糖基浆果赤霉素III
• 英文名称: 7-β-D-xylosylbaccatin III
• 英文别名: 7-Xylosyl-10-deacetylbaccatin III；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,12,15-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 157664-03-4
• 化学式: C₃₄H₄₄O₁₄
• 分子量: 676.715
• InChiKey: PAYIYFPUFSJTDA-HEJNHQNCSA-N

物化性质

• 沸点：
  835.5±65.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  48
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  219
• 氢给体数：
  6
• 氢受体数：
  14

安全信息

• 储存条件：
  存放在2-8℃环境中，应保持干燥并密封。

反应信息

• 作为反应物：
  描述：

  10-O-去乙酰基-7-O-beta-D-吡喃木糖基浆果赤霉素 III 在 Enterobacter sp. CGMCC 2487 作用下， 生成 10-脱乙酰基巴卡丁 III
  参考文献：
  名称：

  Microbial hydrolysis of 7-xylosyl-10-deacetyltaxol to 10-deacetyltaxol

  摘要：

  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 degrees 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. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.11.013
• 作为产物：
  描述：

  7-木糖甙-10-脱乙酰基紫杉醇 生成 10-O-去乙酰基-7-O-beta-D-吡喃木糖基浆果赤霉素 III
  参考文献：
  名称：

  Microbial hydrolysis of 7-xylosyl-10-deacetyltaxol to 10-deacetyltaxol

  摘要：

  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 degrees 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. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2010.11.013
• 作为试剂：
  描述：

  7-Xylosyl-10-deacetyltaxol 、 甲醇 、 Tripotassium;phosphate 在 solution 、 10-O-去乙酰基-7-O-beta-D-吡喃木糖基浆果赤霉素 III 、 Tripotassium;phosphate 、 二氯甲烷 、 甲醇 、 7-Xylosyl-10-deacetyltaxol 作用下， 以 水 为溶剂， 反应 56.0h， 生成 10-O-去乙酰基-7-O-beta-D-吡喃木糖基浆果赤霉素 III
  参考文献：
  名称：

  Enzymatic hydrolysis method for the conversion of C-7 sugar to C-7

  摘要：

  一种酶解法，其中将一个或多个C-7糖，优选为C-7含有木聚糖基团的紫杉醇与能够水解该糖基团为羟基基团的酶或微生物接触。

  公开号：

  US05700669A1

文献信息

• Process for the preparation of 10-deacetylbaccatin III
  申请人：Council of Scientific and Industrial Research

  公开号：US06437154B1

  公开（公告）日：2002-08-20

  The present invention discloses a process for the conversion of a mixture of taxol analogues 7-xylosyl-10-deacetylbaccatin taxols of the formula 2 where R is C6H5, CH3C═CHCH3 or C5H11 into 10-deacetylbaccatin III of the formula 1 by dissolving the taxol analogue of formula 2 in a polar solvent, reacting the resultant solution with a base at a temperature of 20-50° C. for a time period in the range of 20-40 hours, and isolating 7-xyloxyl-10-deacetylbaccatin III, dissolving the 7-xylosyl-10-deacetylbaccatin III in a polar solvent, reacting the resultant solution with a periodate at 20-40° C. for a time period in the range of 20-40 hours to cleave the diol system of the xyloside into dialdehyde, treating the generated dialdehyde in an organic acid medium with salts of amine at 0-40° C. for 12-18 hours and isolating 10-deacetylbaccatin III of formula 1.

  本发明揭示了一种将7-木糖基-10-去乙酰基紫杉醇类似物混合物转化为式2中R为C6H5、CH3C═CHCH3或C5H11的10-去乙酰基巴卡宁III的方法，其中通过将式2的紫杉醇类似物溶解在极性溶剂中，在20-50℃的温度下与碱反应20-40小时，分离出7-木糖氧基-10-去乙酰基巴卡宁III，然后将7-木糖基-10-去乙酰基巴卡宁III溶解在极性溶剂中，在20-40℃的温度下与高碘酸盐反应20-40小时，将木糖苷的双醇系统裂解为双醛，将生成的双醛在有机酸介质中与胺盐在0-40℃的温度下处理12-18小时，分离出式1的10-去乙酰基巴卡宁III。
• NOVEL GLYCOSYL HYDROLASE WITH BETA-XYLOSIDASE AND BETA-GLUCOSIDASE ACTIVITIES AND USES THEREOF
  申请人：Zhu Ping

  公开号：US20130130330A1

  公开（公告）日：2013-05-23

  A novel glycosyl hydrolase with activities of beta-xylosidase and beta-glucosidase is provided. Said glycosyl hydrolase can convert 7-xylosyltaxane compounds to 7-hydroxyltaxane compounds.

  提供了一种新型的糖基水解酶，具有β-木糖苷酶和β-葡萄糖苷酶的活性。该糖基水解酶可以将7-木糖基紫杉烷类化合物转化为7-羟基紫杉烷类化合物。
• Glycosyl hydrolase with beta-xylosidase and beta-glucosidase activities and uses thereof
  申请人：Zhu Ping

  公开号：US09206405B2

  公开（公告）日：2015-12-08

  A novel glycosyl hydrolase with activities of beta-xylosidase and beta-glucosidase is provided. Said glycosyl hydrolase can convert 7-xylosyltaxane compounds to 7-hydroxyltaxane compounds.

  提供了一种新型的糖基水解酶，具有β-木糖苷酶和β-葡萄糖苷酶的活性。该糖基水解酶可以将7-木糖基紫杉烷化合物转化为7-羟基紫杉烷化合物。
• Microbial hydrolysis of 7-xylosyl-10-deacetyltaxol to 10-deacetyltaxol
  作者：Kang Wang、Tingting Wang、Jianhua Li、Jianhua Zou、Yongqin Chen、Jungui Dai

  DOI：10.1016/j.molcatb.2010.11.013

  日期：2011.3

  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 degrees 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. (C) 2010 Elsevier B.V. All rights reserved.
• Enzymatic hydrolysis method for the conversion of C-7 sugar to C-7
  申请人：Bristol-Myers Squibb Company

  公开号：US05700669A1

  公开（公告）日：1997-12-23

  An enzymatic hydrolysis method, wherein one or more C-7 sugar, preferably C-7 xylosyl-bearing taxanes are contacted with an enzyme or microorganism capable of hydrolyzing said sugar groups to hydroxyl groups.

  一种酶解法，其中将一个或多个C-7糖，优选为C-7含有木聚糖基团的紫杉醇与能够水解该糖基团为羟基基团的酶或微生物接触。