propyl (S)-3-hydroxybutanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: propyl (S)-3-hydroxybutanoate
• 英文别名: propyl (3S)-3-hydroxybutanoate；(S)-propyl 3-hydroxybutanoate；(s)-Propyl-3-hydroxybutanoate
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: DYIMQAHDHMHISM-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酸正丙酯 在 葡萄糖 、 三羟甲基氨基甲烷盐酸盐 作用下， 反应 48.0h， 以18%的产率得到propyl (S)-3-hydroxybutanoate
  参考文献：
  名称：

  用面包酵母中的酶不对称还原 β-酮酯

  摘要：

  各种 β-酮酯已被从面包酵母中分离出的一种 β-酮酯还原酶还原。相应的β-羟基酯分别以极好的对映体和非对映体过量获得。还阐明了还原酶不仅识别 β-碳上的立体化学，而且识别 α-碳上的立体化学，主要提供 α-取代的 β-羟基酯的四种可能的非对映异构体之一。立体选择性非常好，化学收率中等至良好。

  DOI：

  10.1246/bcsj.67.524

文献信息

• Poly(3-hydroxybutyrate)-depolymerase from <i>Pseudomonas lemoignei</i>:  Catalysis of Esterifications in Organic Media
  作者：Ajay Kumar、R. A. Gross、D. Jendrossek

  DOI：10.1021/jo000814y

  日期：2000.11.1

  lemoignei in organic media to catalyze ester-forming reactions was investigated. The effect of different organic solvents (benzene-d(6), cyclohexane-d(12), and acetonitrile-d(3)) on the activity of the PHB-depolymerase toward propylation of L-lactide was studied. A significant difference in the catalytic rate was observed as a function of solvent polarity. The selectivity of the PHB-depolymerase (P. lemoignei)

  非水介质中的脂肪酶催化被认为是有机和最近的聚合物合成中的有力工具。即使目前已知的多羟基链烷酸酯（PHA）解聚酶均不具有脂肪酶活性，但它们的催化中心确实类似于脂肪酶。由于以上原因，研究了在有机介质中使用来自肺炎单胞菌的聚（3-羟基丁酸酯），PHB，解聚酶催化酯形成反应的潜力。研究了不同的有机溶剂（苯-d（6），环己烷-d（12）和乙腈-d（3））对PHB解聚酶对L-丙交酯丙基化的活性的影响。观察到催化速率的显着差异是溶剂极性的函数。PHB解聚酶的选择性（P. 已使用PHB解聚酶（Lemoignei）在有机物中研究了催化ε-己内酯，δ-丁内酯，γ-丁内酯，D，L，内消旋和外消旋丙交酯等一系列不同内酯的丙基化反应。溶剂。观察到这些内酯的反应性以及立体化学上不同的线性乳酸二聚体的选择性水解的重要差异。而且，研究了PHB解聚酶催化ε-己内酯和碳酸三亚甲基酯的无溶剂聚合的能力。还观察到了立体化学上不同
• Biochemical Reduction of 3-Oxoalkanoic Esters by a Bottom-fermentation Yeast,<i>Saccharomyces cerevisiae</i>IFO 0565
  作者：Naoki Mochizuki、Takeshi Sugai、Hiromichi Ohta

  DOI：10.1271/bbb.58.1666

  日期：1994.1

  The scope and limitation of a bottom-fermentation yeast (Saccharomyces cerevisiae IFO 0565) toward the reduction of 3-oxoalkanoic esters were examined. The substrate specificity of this microorganism for various kinds of 3-oxoalkanoic esters was studied. This microorganism was distinct from converntional bakers’ yeast in terms of its selectivity in the reduction and its high expression of a hydrolytic enzyme. 3-Oxoalkanoic ester with an aromatic substituent, a halogen substituted 3-oxoalkanoic ester, an aliphatic longer-chain 3-oxoalkanoic ester and its α,α-difluoro analog were also accepted by this microorganism. The products are useful intermediates in the synthesis of physiologically active compounds.

  研究了底发酵酵母（酿酒酵母 Saccharomyces cerevisiae IFO 0565）在还原3-氧杂烷酸酯方面的范围和局限性。对该微生物对各种3-氧杂烷酸酯的底物特异性进行了研究。该微生物在还原选择性以及水解酶的高表达方面明显不同于传统的烘焙酵母。具有芳香取代基的3-氧杂烷酸酯、卤代3-氧杂烷酸酯、脂肪族长链3-氧杂烷酸酯及其α,α-二氟类似物也被该微生物接受。这些产品是合成生理活性化合物的有用中间体。
• Asymmetric Reduction of<i>β</i>-Keto Esters with an Enzyme from Bakers’ Yeast
  作者：Yasushi Kawai、Munekazu Tsujimoto、Shin-ichi Kondo、Kousuke Takanobe、Kaoru Nakamura、Atsuyoshi Ohno

  DOI：10.1246/bcsj.67.524

  日期：1994.2

  Various β-keto esters have been reduced by one of β-keto ester reductases isolated from bakers’ yeast. The corresponding β-hydroxy esters have been obtained in excellent enantiomeric and diastereomeric excesses, respectively. It has also been elucidated that the reductase recognizes the stereochemistry not only at the β-carbon but also at the α-carbon affording one of the four possible diastereoisomers

  各种 β-酮酯已被从面包酵母中分离出的一种 β-酮酯还原酶还原。相应的β-羟基酯分别以极好的对映体和非对映体过量获得。还阐明了还原酶不仅识别 β-碳上的立体化学，而且识别 α-碳上的立体化学，主要提供 α-取代的 β-羟基酯的四种可能的非对映异构体之一。立体选择性非常好，化学收率中等至良好。
• Asymmetric visible-light photobiocatalytic reduction of β-keto esters utilizing the cofactor recycling system in Synechocystis sp. PCC 6803
  作者：Shusei Tanaka、Hideo Kojima、Satomi Takeda、Rio Yamanaka、Tetsuo Takemura

  DOI：10.1016/j.tetlet.2020.151973

  日期：2020.6

  The asymmetric reduction of beta-keto esters employing a wild-type strain of cyanobacterium Synechocystis sp. PCC 6803 under illumination of red LED light at 25 degrees C for 24 h was evaluated. As a result, the corresponding (R)-beta-hydroxy esters were obtained as major products. The R-selectivity was shown to increase for bulkier substrates. Moreover, it was also found that the R-selectivity increased with decreasing substrate concentrations. This can be explained by the assumption that the Km value of the R-selective reductase is smaller than that of the S-selective enzyme involved in the reaction. Additionally, it was demonstrated that the R-selective reductase required the light-dependent production of reduced nicotinamide adenine dinucleotide phosphate (NADPH) for effective reaction; however, the S-selective variant did not. Overall, cyanobacterium was employed as a sustainable photobiocatalyst proliferating under illumination of light, while utilizing inorganic salts and atmospheric carbon dioxide (CO2). Employing the whole-cell system allowed for the preparation of industrially-important chiral compounds, such as optically active beta-hydroxy esters. (C) 2020 Elsevier Ltd. All rights reserved.
• Single‐Point Mutant Inverts the Stereoselectivity of a Carbonyl Reductase toward β‐Ketoesters with Enhanced Activity
  作者：Aipeng Li、Ting Wang、Qing Tian、Xiaohong Yang、Dongming Yin、Yong Qin、Lianbing Zhang

  DOI：10.1002/chem.202005195

  日期：2021.4.7

  Enzyme stereoselectivity control is still a major challenge. To gain insight into the molecular basis of enzyme stereo‐recognition and expand the source of antiPrelog carbonyl reductase toward β‐ketoesters, rational enzyme design aiming at stereoselectivity inversion was performed. The designed variant Q139G switched the enzyme stereoselectivity toward β‐ketoesters from Prelog to antiPrelog, providing

  酶的立体选择性控制仍然是主要挑战。为了深入了解酶立体识别的分子基础，并将antiPrelog羰基还原酶的来源扩展至β-酮酸酯，进行了针对立体选择性反转的合理酶设计。设计的Q139G变体将酶对β-酮酸酯的立体选择性从Prelog切换为antiPrelog，从而提供了相应的具有高对映体纯度（89.1–99.1％ee）的醇。更重要的是，在立体选择性和活性之间未找到众所周知的折衷方案。Q139G表现出比野生型酶更高的催化活性，提高了催化效率（k cat / K m）从1.1到27.1倍不等。有趣的是，突变体Q139G并未导致对芳族酮的立体选择性反转。酶-底物复合物的分析表明，β-酮酸酯的结构柔韧性和新形成的空穴共同促进了抗Prelog-首选构象的形成。相比之下，芳族酮的相对较大和刚性的结构阻止了它们形成抗Prelog优先的构象。