(S)- ((ethylsulfinyl)methyl)benzene | 70286-60-1

• 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: (S)- ((ethylsulfinyl)methyl)benzene
• 英文别名: (S)-benzyl ethyl sulfoxide；Benzene, [[(S)-ethylsulfinyl]methyl]-；[(S)-ethylsulfinyl]methylbenzene
• CAS: 70286-60-1
• 化学式: C₉H₁₂OS
• 分子量: 168.26
• InChiKey: KCXODFMHDFXFSV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苄基乙基硫醚 在 glucose-6-phosphate dehydrogenase 、 Α-D-吡喃葡萄糖6-磷酸 、 Thermobifida fusca phenylacetone monooxygenase 、 nicotinamide adenine dinucleotide phosphate 作用下， 反应 6.0h， 生成 (S)- ((ethylsulfinyl)methyl)benzene
  参考文献：
  名称：

  [Cp * Rh（bpy）（H2O）] 2+作为由Baeyer-Villiger单加氧酶催化的酶氧化中的辅酶替代物。

  摘要：

  [Cp * Rh（bpy）（H2O）] 2+用作黄素再生试剂，用于BVMO催化的有机硫化物氧化为手性亚砜。

  DOI：

  10.1039/b504921k

文献信息

• Enzymatic kinetic resolution of chiral sulfoxides – an enantiocomplementary approach
  作者：Vladimír Nosek、Jiří Míšek

  DOI：10.1039/c9cc05470g

  日期：——

  A new enzymatic assay for the preparation of chiral sulfoxides that is enantiocomplementary to the known (S)-enantiomer-reducing activity of methionine sulfoxide reductase A (MsrA) is described. To this end, we have utilized the enzyme DMSO reductase (DmsABC), recently discovered by us being highly upregulated in stationary phase E. coli bacteria.

  描述了一种新的用于制备手性亚砜的酶促测定方法，该方法与甲硫氨酸亚砜还原酶A（MsrA）的已知的（S）-对映异构体还原活性是对映体互补的。为此，我们利用了DMSO还原酶（DmsABC），该酶最近被我们发现在固定相大肠杆菌中高度上调。
• Turning a riboflavin-binding protein into a self-sufficient monooxygenase by cofactor redesign
  作者：Gonzalo de Gonzalo、Christian Smit、Jianfeng Jin、Adriaan J. Minnaard、Marco W. Fraaije

  DOI：10.1039/c1cc14039f

  日期：——

  By cofactor redesign, self-sufficient monooxygenases could be prepared. Tight binding of N-alkylated flavins to riboflavin-binding protein results in the creation of artificial flavoenzymes capable of H2O2-driven enantioselective sulfoxidations. By altering the flavin structure, opposite enantioselectivities could be achieved, in accordance with the binding mode predicted by in silicoflavin-protein docking of the unnatural flavin cofactors. The study shows that cofactor redesign is a viable approach to create artificial flavoenzymes with unprecedented activities.

  通过辅因子重设计，可以制备自给自足的单氧化酶。N-烷基化黄素与核黄素结合蛋白的紧密结合会产生能够驱动过氧化氢进行对映选择性亚磺氧化反应的人工黄酶。通过改变黄素结构，可以实现相反的对映选择性，这与通过计算机模拟的不天然黄素辅因子的结合模式预测一致。该研究表明，辅因子重设计是一种创造具有前所未有活性的人工黄酶的可行方法。
• Exploring the biocatalytic scope of a bacterial flavin-containing monooxygenase
  作者：Ana Rioz-Martínez、Malgorzata Kopacz、Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Vicente Gotor、Marco W. Fraaije

  DOI：10.1039/c0ob00988a

  日期：——

  A bacterial flavin-containing monooxygenase (FMO), fused to phosphite dehydrogenase, has been used to explore its biocatalytic potential. The bifunctional biocatalyst could be expressed in high amounts in Escherichia coli and was able to oxidize indole and indole derivatives into a variety of indigo compounds. The monooxygenase also performs the sulfoxidation of a wide range of prochiral sulfides, showing moderate to good enantioselectivities in forming chiral sulfoxides.

  一种含黄素的单氧化酶（FMO）与磷酸脱氢酶融合，被用于探索其生物催化潜力。这种双功能生物催化剂能够在大肠杆菌中高量表达，并能够将吲哚及其衍生物氧化成多种靛蓝化合物。该单氧化酶还对多种前手性硫化物进行亚硫氧化，显示出中等到良好的选择性，能够形成手性亚硫氧化物。
• 4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB as an oxidative biocatalyst in the synthesis of optically active sulfoxides
  作者：Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Gianluca Ottolina、Marco W. Fraaije、Giacomo Carrea

  DOI：10.1016/j.tetasy.2005.11.024

  日期：2006.1

  sulfoxidation reactions on a set of aromatic sulfides. With a few exceptions, excellent enantioselectivities in the synthesis of chiral phenyl and benzyl sulfoxides were achieved. The bacterial Baeyer–Villiger monooxygenase was also shown to accept racemic sulfoxides, a prochiral diketone and an organoboron compound as substrates. This study demonstrates the great biocatalytic potential of this novel oxidative

  来自荧光假单胞菌ACB的重组4-羟基苯乙酮单加氧酶（HAPMO）已作为一组芳族硫化物的硫氧化反应的催化剂进行了测试。除少数例外，在手性苯基和苄基亚砜的合成中获得了极好的对映选择性。细菌Baeyer-Villiger单加氧酶也被证明可以接受外消旋亚砜，前手性二酮和有机硼化合物作为底物。这项研究证明了这种新型氧化酶的巨大生物催化潜力。
• [Cp*Rh(bpy)(H2O)]2+ as a coenzyme substitute in enzymatic oxidations catalyzed by Baeyer–Villiger monooxygenases
  作者：Gonzalo de Gonzalo、Gianluca Ottolina、Giacomo Carrea、Marco W. Fraaije

  DOI：10.1039/b504921k

  日期：——

  [Cp*Rh(bpy)(H2O)]2+ was applied as a flavin regenerating reagent in BVMO catalyzed oxidations of organic sulfides to chiral sulfoxides.

  [Cp * Rh（bpy）（H2O）] 2+用作黄素再生试剂，用于BVMO催化的有机硫化物氧化为手性亚砜。