(4S,6R)-6-(tert-butyldimethylsilyloxy)-7-phenylhept-1-en-4-ol | 1374151-69-5

• 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: (4S,6R)-6-(tert-butyldimethylsilyloxy)-7-phenylhept-1-en-4-ol
• CAS: 1374151-69-5
• 化学式: C₁₉H₃₂O₂Si
• 分子量: 320.547
• InChiKey: SRHFMANXQDDWJB-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4S,6R)-6-(tert-butyldimethylsilyloxy)-7-phenylhept-1-en-4-ol 在 咪唑 、 4-二甲氨基吡啶 、 potassium permanganate 、 sodium periodate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 0.08h， 生成 methyl 7-((3R,5R)-3,5-bis(tert-butyldimethylsilyloxy)-6-phenylhexanamido)heptanoate
  参考文献：
  名称：

  6-Deoxyerythronolide B Synthase Thioesterase-Catalyzed Macrocyclization Is Highly Stereoselective

  摘要：

  Macrocyclic polyketide natural products are an indispensable source of therapeutic agents. The final stage of their biosynthesis, macrocyclization, Is catalyzed regio- and stereoselectively by a thioesterase. A panel of substrates were synthesized to test their specificity for macrocyclization by the erythromycin polyketide synthase TE (DEBS TE) in vitro. It was shown that DEBS TE is highly stereospecific, successfully macrocyclizing a 14-member ring substrate with an R configured O-nucleophile, and highly regioselective, generating exclusively the 14-member lactone over the 12-member lactone.

  DOI：

  10.1021/ol300707j
• 作为产物：
  描述：

  在 copper(l) iodide 、 (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III) 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 16.33h， 生成 (4S,6R)-6-(tert-butyldimethylsilyloxy)-7-phenylhept-1-en-4-ol
  参考文献：
  名称：

  6-Deoxyerythronolide B Synthase Thioesterase-Catalyzed Macrocyclization Is Highly Stereoselective

  摘要：

  Macrocyclic polyketide natural products are an indispensable source of therapeutic agents. The final stage of their biosynthesis, macrocyclization, Is catalyzed regio- and stereoselectively by a thioesterase. A panel of substrates were synthesized to test their specificity for macrocyclization by the erythromycin polyketide synthase TE (DEBS TE) in vitro. It was shown that DEBS TE is highly stereospecific, successfully macrocyclizing a 14-member ring substrate with an R configured O-nucleophile, and highly regioselective, generating exclusively the 14-member lactone over the 12-member lactone.

  DOI：

  10.1021/ol300707j

文献信息

• Towards a characterization of the structural determinants of specificity in the macrocyclizing thioesterase for deoxyerythronolide B biosynthesis
  作者：Panos Argyropoulos、Fabien Bergeret、Christophe Pardin、Janice M. Reimer、Atahualpa Pinto、Christopher N. Boddy、T. Martin Schmeing

  DOI：10.1016/j.bbagen.2015.11.007

  日期：2016.3

  Type I polyketide synthases (PKSs) are giant multidomain proteins that synthesize many therapeutics and other natural products. The synthesis proceeds by a thiotemplate mechanism whereby intermediates are covalently attached to the PKS. The release of the final polyketide is catalyzed by the terminal thioesterase (TE) domain through hydrolysis, transesterification, or macrocyclization. The PKS 6-deoxyerythronolide

  I型聚酮化合物合酶（PKS）是巨大的多域蛋白，可合成许多治疗剂和其他天然产物。合成通过硫代模板机理进行，其中中间体共价附于PKS。最终的聚酮化合物的释放是通过末端硫酯酶（TE）域通过水解，酯交换或大环化来催化的。PKS 6-脱氧赤藓醇B合酶（DEBS）产生具有临床意义的抗生素红霉素的14元大环内酯核心。DEBS的TE结构域（DEBS TE）对天然和修饰底物的水解或大环化具有公认的，经验确定的特异性。我们目前正在努力了解使用一组新颖的二苯基烷基膦酸酯在DEBS TE中硫酯酶反应特异性的结构基础，模拟由DEBS TE专门环化或水解的底物。我们已经确定了仅在1.7Å处的DEBS TE的新构建体的结构，并且以2.1Å的分辨率与简单的烯丙基膦酸酯结合的DEBS TE。其他更复杂的二苯基烷基膦酸酯会抑制DEBS TE，但我们无法可视化这些与DEBS TE配合的忠实环化类似物。这项工作代表着使用与复杂底物类似物复合的DEBS