(-)-(S)-3-hydroxyindolin-2-one | 957472-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (-)-(S)-3-hydroxyindolin-2-one
• 英文别名: (3S)-3-hydroxy-1,3-dihydroindol-2-one
• CAS: 957472-95-6
• 化学式: C₈H₇NO₂
• 分子量: 149.149
• InChiKey: SGZFJWQQBHYNNF-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-amino-L-mandelic acid 在 硫酸 作用下， 生成 (-)-(S)-3-hydroxyindolin-2-one
  参考文献：
  名称：

  23.吲哚基团的旋光性

  摘要：

  DOI：

  10.1039/jr9350000104

文献信息

• Two Enantiocomplementary Ephedrine Dehydrogenases from <i>Arthrobacter</i> sp. TS-15 with Broad Substrate Specificity
  作者：Tarek Shanati、Cameron Lockie、Lilian Beloti、Gideon Grogan、Marion B. Ansorge-Schumacher

  DOI：10.1021/acscatal.9b00621

  日期：2019.7.5

  The recently identified pseudoephedrine and ephedrine dehydrogenases (PseDH and EDH, respectively) from Arthrobacter sp. TS-15 are NADH-dependent members of the oxidoreductase superfamily of short-chain dehydrogenases/reductases (SDRs). They are specific for the enantioselective oxidation of (+)-(S) N-(pseudo)ephedrine and (−)-(R) N-(pseudo)ephedrine, respectively. Anti-Prelog stereospecific PseDH

  最近从节杆菌属中鉴定出的伪麻黄碱和麻黄碱脱氢酶（分别为PseDH和EDH）。TS-15是短链脱氢酶/还原酶（SDR）氧化还原酶超家族的NADH依赖性成员。它们分别对（+）-（S）N-（伪）麻黄碱和（-）-（R）N-（伪）麻黄碱的对映选择性氧化具有特异性。抗Prelog立体特异性PseDH和Prelog特异性EDH催化1-苯基-1,2-丙二酮向（S）-苯基乙酰甲醇和（R的区域和对映体特异性还原）-苯基乙酰基甲醇，具有完全转化率，对映体过量> 99％。此外，它们将包括芳胺，酮酸酯和卤代酮在内的各种芳基-脂族羰基化合物还原为相应的对映纯醇。确定PseDH和EDH的最高稳定性分别在6.0-8.0和7.5-8.5的pH范围内。在25°C下，PseDH比EDH更稳定，半衰期分别为279和38 h。但是，EDH在40°C时更稳定，半衰期比25°C时长两倍。精制至1.83Å分辨率的PseDH–NAD +配
• Enantioselective bioreduction of benzo-fused cyclic ketones with engineered Candida glabrata ketoreductase 1 – a promising synthetic route to ladostigil (TV3326)
  作者：Jingping Ou-yang、Wenhe Zhang、Fengyu Qin、Weiguo Zuo、Shaoyu Xu、Yan Wang、Bin Qin、Song You、Xian Jia

  DOI：10.1039/c7ob01803g

  日期：——

  Biocatalysis has been recently emerging as a promising alternative to traditional chemical synthesis because of its “green” characteristics and comparable selectivities, which accord with the concept of sustainable development and demand for asymmetric synthesis. In this study, whole-cell biocatalysts containing glucose dehydrogenase (GDH) and Candida glabrata ketoreductase 1 (CgKR1) variants were

  生物催化由于其“绿色”特性和可比的选择性，符合可持续发展的概念和对不对称合成的需求，最近已成为一种有希望的替代传统化学合成方法。在这项研究中，构建了包含葡萄糖脱氢酶（GDH）和光滑念珠菌酮还原酶1（CgKR1）变体的全细胞生物催化剂。这些生物催化剂被用于还原苯并稠合的环酮，并表现出良好的活性至高的对映选择性。特别是，CgKR1变体对ladostigil（TV3326）的关键中间体5a表现出高活性（90.6％–98.4％转化）和对映选择性（> 99.9％ee ）。根据这些结果，化学酶法合成（通过使用生物催化不对称还原作为关键步骤开发了S）-5b，得到的产品的总收率为34.0％和ee的99.9％。
• (S)-specific carbonyl reductase from Candida parapsilosis ATCC 7330 as a model for the initial screening of inhibitors for human carbonyl reductase
  作者：K. Leena、Sathyanarayana N. Gummadi、Anju Chadha

  DOI：10.1016/j.bej.2023.109205

  日期：2024.3

  Human carbonyl reductase (CBR1) reduces carbonyl groups in drug molecules, particularly anticancer drugs, leading to altered pharmacological effects. This study reports a simple and efficient system that utilizes enzymes isolated from yeast as a model for the initial screening of inhibitors for human carbonyl reductases, offering a viable process for large scale applications. A purified stereospecific

  人羰基还原酶(CBR1) 会减少药物分子（尤其是抗癌药物）中的羰基，从而导致药理作用发生改变。这项研究报告了一种简单而有效的系统，该系统利用从酵母中分离的酶作为人类羰基还原酶抑制剂的初步筛选模型，为大规模应用提供了可行的方法。采用纯化的立体特异性酶，即来自近平滑假丝酵母ATCC 7330 (SRED) 的 ( S ) 特异性羰基还原酶，其晶体结构 PDB ID：3CTM（与 SRED 100% 序列同一性）显示与 CBR1（PDB ID：1WMA）有 27% 相似性）。此外，还发现它与靛红的反应和与槲皮素的抑制（非竞争性）与 CBR1具有相似性。靛红作为底物的K m为 5.3 ± 1.08 mM，槲皮素作为抑制剂的K i为 15.2 ± 1.64 µM。使用 ( S ) 特异性羰基还原酶模型酶，鉴定出一种新型抑制剂，乙基 (E)−4-(4-氯苯基)−2-氧代丁-3-烯酸乙酯 (ECOB)。ECOB
• Biotechnological Properties of Sponges from Northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds
  作者：Valéria Riatto、Mauricio Victor、Jaqueline Sousa、Carla Menegola

  DOI：10.21577/0103-5053.20180165

  日期：——

  To research the potential ability of whole marine sponges to act as biocatalysts, this paper describes for the first time the employment of whole Cliona varians sponge in the stereoselective reduction of prochiral alpha-keto esters and isatin to the corresponding chiral alcohols. The addition of D-fructose, D-glucose or sucrose remarkably increased the conversion ratios and stereoselectivities by this marine sponge. Furthermore, in the presence of D-glucose and D-maltose. the reduction of isatin by C. varians afforded the corresponding 3-hydroxyindolin-2-one with high conversions (85-90%) and good enantioselectivities (60-74%). These results showed that the marine sponge presents great potential to be used as biocatalyst for stereoselective reduction of carbonyl compounds.
• First Asymmetric Reduction of Isatin by Marine-Derived Fungi
  作者：Willian Birolli、Irlon Ferrreira、David Jimenez、Bianca Silva、Bárbara Silva、Angelo Pinto、André Porto

  DOI：10.21577/0103-5053.20160256

  日期：——

  In this study, whole cells of marine-derived fungi were used to reduce isatin (1H-indole2,3-dione) to dioxindole (3-hydroxyindolin-2-one) for 7 days at 32 degrees C. The screening showed that several strains could reduce isatin and produce the enantioenriched dioxindole. The best conversions were obtained by Cladosporium sp. CBMAI 1237 and Westerdykella sp. CBMAI 1679, however, the best enantiomeric excess was obtained only by Aspergillus sydowii CBMAI 935 (66% ee). In conclusion, marine-derived fungi show potential for asymmetric and chemoselective reduction of isatin (1H-indole-2,3-dione).