(S)-3-Hydroxybutansaeurebutylester | 61597-99-7

• 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: (S)-3-Hydroxybutansaeurebutylester
• 英文别名: (S)-butyl 3-hydroxybutanoate；Butyl (3S)-3-hydroxybutanoate
• CAS: 61597-99-7
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: LHDWRKCOQQHAMP-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-Hydroxybutansaeurebutylester 、 碘甲烷 在 lithium diisopropyl amide 作用下， 生成 Butyl 3-hydroxy-2-methylbutanoate
  参考文献：
  名称：

  Tai, Akira; Morimoto, Naotake; Yoshikawa, Masato, Agricultural and Biological Chemistry, 1990, vol. 54, # 7, p. 1753 - 1762

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸正丁酯 在 Baeckerhefe 、 蔗糖 作用下， 以 水 为溶剂， 反应 96.0h， 以58%的产率得到(S)-3-Hydroxybutansaeurebutylester
  参考文献：
  名称：

  关于聚（R）-3-羟基丁酸酯（PHB）的解聚

  摘要：

  关于聚（R）-3-羟基丁酸酯（PHB）的解聚

  DOI：

  10.1002/hlca.19820650208

文献信息

• 3-Deoxyglucosone Reductase in Dog Adrenal Glands. Identification as Aldose Reductase.
  作者：Kazuya MATSUURA、Kumiko SATO、Yoshihiro DEYASHIKI、Masayuki NAKANISHI、Akira HARA

  DOI：10.1248/bpb.18.1765

  日期：——

  3-Deoxyglucosone is one of the major cytotoxic intermediates in the Maillard reaction. Adrenal glands showed the highest NADPH-linked 3-deoxyglucosone reductase activity of dog tissues. The enzyme was purified to homogeneity from the adrenal glands, and demonstrated to be structurally, functionally and immunologically identical with aldose reductase, which comprises about 6% of the soluble adrenal proteins.

  3-脱氧葡萄糖酮是迈拉德反应中主要的细胞毒性中间产物之一。肾上腺显示出狗组织中最高的NADPH依赖性3-脱氧葡萄糖酮还原酶活性。该酶从肾上腺中被纯化至均一状态，并被证明在结构上、功能上以及免疫学上与醛糖还原酶相同，后者约占肾上腺可溶性蛋白质的6%。
• Aliphatic β-d-glucosides from fruits of Carica pubescens
  作者：Doris Krajewski、Carmenza Duque、Peter Schrejer

  DOI：10.1016/s0031-9422(97)00196-9

  日期：1997.8

  Abstract Ethyl 3- O -β- d -glucopyranosylbutanoate, butyl 3- O -β- d -glucopyranosylbutanoate and 3-oxo-octyl 1- O -β- d -glucopyranoside were isolated from Carica pubescens fruit pulp by liquid chromatography on XAD. Identifications were performed after peracetylation by comparison of HRGC and HRGC-mass spectral data with those of synthesized reference compounds. Chiral evaluation of glycosidically-bound

  摘要 采用XAD液相色谱法从毛竹果肉中分离得到3-O-β-d-吡喃葡萄糖基丁酸乙酯、3-O-β-d-吡喃葡萄糖基丁酸丁酯和3-氧辛基1-O-β-d-吡喃葡萄糖苷。通过将 HRGC 和 HRGC 质谱数据与合成参考化合物的数据进行比较，在全乙酰化后进行鉴定。通过多维气相色谱，将极性非手性柱 (DB-Wax) 与手性主柱 (heptakis-2,6-di-O -甲基-3-O-戊基-β-环糊精/OV 1701 和 2, 3-二-O-乙酰基-6-O-叔丁基-二甲基甲硅烷基-β-环糊精/OV 1701）。合成的保留时间比较，具有酶促释放苷元的光学富集参考化合物显示(S)-3-羟基丁酸酯的对映体过量，即乙酯和丁酯分别为96%和24%。辛烷-1,3-二醇表现出 ( R )-90% 的对映体过量。© 1997 Elsevier Science Ltd. 版权所有
• 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。
• 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。
• 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.