7,13-O,O-diacetyl-2-O-debenzoyl-2-O-(2-thiophenecarbonyl)baccatin III | 1215640-83-7

• 英文名称: 7,13-O,O-diacetyl-2-O-debenzoyl-2-O-(2-thiophenecarbonyl)baccatin III
• 英文别名: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,9,12,15-tetraacetyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] thiophene-2-carboxylate
• CAS: 1215640-83-7
• 化学式: C₃₃H₄₀O₁₃S
• 分子量: 676.739
• InChiKey: UJWBBYXJACZSAX-XLAATQKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  206
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  7,13-O,O-diacetyl-2-O-debenzoylbaccatin III 、 Thiophene-2-carbonyl-CoA 在 mutant 2-O-debenzoylbaccatin III 2-O-benzoyltransferase, containing point mutations: Q₁₉P and N₂₃K 作用下， 生成 7,13-O,O-diacetyl-2-O-debenzoyl-2-O-(2-thiophenecarbonyl)baccatin III
  参考文献：
  名称：

  Point Mutations (Q19P and N23K) Increase the Operational Solubility of a 2α-O-Benzoyltransferase that Conveys Various Acyl Groups from CoA to a Taxane Acceptor

  摘要：

  Two site-directed Mutations within the wild-type 2-O-benzoyltransferase (tbt) cDNA, from Taxus cuspidata plants, yielded air encoded protein containing replacement amino acids at Q19P and N23K that trial) to a solvent-exposed loop region. The likely significant changes in the biophysical properties invoked by these mutations Caused the overexpressed, modified TBT (mTBT) to partition into the Soluble enzyme fraction about 5-fold greater than the wild-type enzyme. Sufficient protein could now be acquired to examine the scope of the substrate specificity of mTBT by incubation with 7,13-O,O-diacetyl-2-O-debenzoylbaceatin III that was mixed individually with various substituted benzoyls, alkanoyls, and (E)-butenoyl CoA donors. The mTBT catalyzed the conversion of each 7,13-O,O-diacetyl-2-O-debenzoylbaccatin III to several 7,13-O,O-diacetyl-2-O-acyl-2-O-debenzoylbaccatin III analogues. The relative catalytic efficiency of mTBT with the 7,13-O,O-diacetyl-2-O-debenzoyl surrogate Substrate and heterole carbonyl CoA substrates was slightly greater than with the natural aroyl substrate benzoyl CoA, While substituted benzoyl CoA thioesters were less productive. Short-chain hydrocarbon carbonyl and cyclohexanoyl CoA thioesters were also productive, where C-4 Substrates were transferred by mTBT with similar to 10- to 17-fold greater catalytic efficiency compared to the transfer of benzoyl. The described broad specificity of mTBT suggests (flat a plethora of 2-O-acyl variants of the antimitotic paclitaxel can be assembled through biocatalytic sequences.

  DOI：

  10.1021/np900524d