ethyl phenylacetyl carbonate | 21260-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl phenylacetyl carbonate
• 英文别名: Phenylessigsaeure--anhydrid；Phenylessigsaeure-(aethylkohlensaeure)-anhydrid；Ethoxycarbonyl 2-phenylacetate
• CAS: 21260-92-4
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: QPYOHKSQOOSQHP-UHFFFAOYSA-N

物化性质

• 沸点：
  295.8±33.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl phenylacetyl carbonate 、 coenzyme A disodium salt 在 碳酸氢钠 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.5h， 以15 mg的产率得到[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-2-[[羟基-[羟基-[3-羟基-2,2-二甲基-3-[2-[2-(2-苯基乙酰基)硫基乙基氨基甲酰]乙基氨基甲酰]丙氧基]磷酰]氧基-磷酰]氧基甲基]四氢呋喃-3-基]氧基膦酸
  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
• 作为产物：
  描述：

  苯乙酸 、 氯甲酸乙酯 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl phenylacetyl carbonate
  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

文献信息

• Synthesis, characterization and potential application of monoacyl-cyclodextrins
  作者：Katia Martina、Devendra Sharad Puntambekar、Alessandro Barge、Marina Gallarate、Daniela Chirio、Giancarlo Cravotto

  DOI：10.1016/j.carres.2009.11.009

  日期：2010.1

  Although the preparation of cyclodextrin (CD) monoesters with a variety of carboxylic acids has been already described in the literature, the direct regioselective CD acylation has proved to be critical often, requiring to be replaced with a more elaborate synthetic process. In this paper we describe the one-step preparation of several monoacylated CDs from acyclic or aromatic carboxylic acid derivatives. The ability of beta-CD to enclose cupric ions in a sandwich-type manner was exploited to lead to high regioselectivity in the acylation of beta-CD with benzoyl chloride, cinnamoyl chloride and phenyl acetyl chloride in water. Long chain aliphatic monoesters of alpha-, beta- and gamma-CD were best reared in DMF. The results of our study showed that solvent and general conditions determined an overwhelming regioselectivity of acylation. H-1, C-13 and 2D NMR experiments could easily discriminate the position of the ester. Monoacylated CDs were evaluated as a carrier of silibinin, the inclusion complexes were prepared and characterized by thermal analysis. (C) 2009 Elsevier Ltd. All rights reserved.
• US4735959A
  申请人：——

  公开号：US4735959A

  公开（公告）日：1988-04-05
• Point Mutations (Q19P and N23K) Increase the Operational Solubility of a 2α-<i>O</i>-Benzoyltransferase that Conveys Various Acyl Groups from CoA to a Taxane Acceptor
  作者：Irosha N. Nawarathne、Kevin D. Walker

  DOI：10.1021/np900524d

  日期：2010.2.26

  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.