(R)-(+)-羟基-2-庚酸乙酯 | 111137-20-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (R)-(+)-羟基-2-庚酸乙酯
• 英文名称: ethyl (R)-2-hydroxyheptanoate
• 英文别名: ethyl (2R)-2-hydroxyheptanoate
• CAS: 111137-20-3
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: OCNVZDKHNZUBQB-MRVPVSSYSA-N

物化性质

• 沸点：
  219.7±8.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (R)-(+)-羟基-2-庚酸乙酯 在 2,6-二甲基吡啶 作用下， 以 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 1.0h， 生成 (+)(S)-2-methyl-enanthic acid ethyl ester
  参考文献：
  名称：

  光学活性α-甲酯的立体选择性合成

  摘要：

  可以容易地从相应的酯和三氟甲磺酸酐获得的α-羟基酯的三氟甲磺酸酯与乙醚中的二甲基铜锂或THF中的镁铝酸酯反应，以提供高对映体纯度的α-甲基酯。

  DOI：

  10.1016/0040-4039(90)80095-4
• 作为产物：
  描述：

  乙基(2R)-2,3-环氧树脂丙烷酸酯 生成 (R)-(+)-羟基-2-庚酸乙酯
  参考文献：
  名称：

  LARCHEVEQUE, MARC JEAN MARCEL;PETIT, YVES ROGER EUGENE

  摘要：

  DOI：

文献信息

• Asymmetric Reduction of<i>α</i>-Keto Esters and<i>α</i>-Diketones with a Bakers’ Yeast Keto Ester Reductase
  作者：Yasushi Kawai、Kouichi Hida、Munekazu Tsujimoto、Shin-ichi Kondo、Kazutada Kitano、Kaoru Nakamura、Atsuyoshi Ohno

  DOI：10.1246/bcsj.72.99

  日期：1999.1

  ketones have been synthesized by the reduction of the corresponding ketones with a keto ester reductase isolated from bakers’ yeast (YKER-I). The reduction of α-keto esters affords the corresponding (S)- or (R)-hydroxy esters selectively, where the stereochemical course depends on the chain length of the alkyl substituent on the carbonyl group. An α-keto short alkanoic ester affords the corresponding

  通过用从面包酵母 (YKER-I) 中分离的酮酯还原酶还原相应的酮，合成了光学纯的 α-羟基酯和 α-羟基酮。α-酮酯的还原选择性地提供相应的 (S)-或 (R)-羟基酯，其中立体化学过程取决于羰基上烷基取代基的链长。α-酮基短链烷酸酯生成相应的 (S)-羟基酯，而长链烷酸酯生成相应的 (R)-羟基酯。α-二酮的还原在区域和立体选择性上提供了相应的 (S)-2-羟基酮。
• Reductive biotransformation of carbonyl compounds—application of fungus, Geotrichum sp. G38 in organic synthesis
  作者：Gu Jian-Xin、Li Zu-Yi、Lin Guo-Qiang

  DOI：10.1016/s0040-4020(01)87947-3

  日期：1993.6

  The microbial transformation of 2- and 3-oxo esters and diketones with Geotrichum sp. G38 and its application to the syntheses of the key intermediates of several bioactive compounds such as (R)-denopamine 8, (R)-fluoxetine 11 and (2S, 3R)-sitophilate 14 were described.

  Geotrichum sp对2-和3-氧代酯和二酮的微生物转化。描述了G38及其在几种生物活性化合物如（R）-地巴胺8，（R）-氟西汀11和（2S，3R）-sitophilate 14的关键中间体的合成中的应用。
• Purification and Characterization of Two α-Keto Ester Reductases from<i>Streptomyces thermocyaneoviolaceus</i>IFO 14271
  作者：Hitomi YAMAGUCHI、Nobuyoshi NAKAJIMA、Kohji ISHIHARA

  DOI：10.1271/bbb.66.588

  日期：2002.1

  Two NADPH-dependent α-keto ester reductases (Streptomyces thermocyaneoviolaceus keto ester reductase, STKER-II and -III) were purified from S. thermocyaneoviolaceus IFO 14271, one of thermophilic actinomycetes. The molecular masses of native STKER-II and -III were estimated to be 60 kDa and 70 kDa by gel filtration chromatography, respectively. These enzymes were both homodimers, with 29-kDa and 30-kDa subunit molecular masses based on SDS polyacrylamide gel electrophoresis. STKER-II and -III were stable from pH 7.0 to 10.0 and pH 5.5 to 9.0, respectively. Ethyl 3-methyl-2-oxobutanoate was reduced by both enzymes isolated to the corresponding (R)-hydroxy ester with excellent enantiomeric excess. STKER-III showed high stereoselectivity for the reduction of bulky substrates, while the selectivity of the STKER-II-catalyzed reduction was low except for ethyl 3-methyl-2-hydroxybutanoate. Both enzymes had small Km values toward aliphatic keto esters having a long alkyl chain.

  从嗜热放线菌 S. thermocyaneoviolaceus IFO 14271 中纯化了两种 NADPH 依赖的 α-酮酯还原酶（Streptomyces thermocyaneoviolaceus 酮酯还原酶 STKER-II 和 -III）。通过凝胶过滤色谱法，测得原形态 STKER-II 和 -III 的分子量分别为 60 kDa 和 70 kDa。根据 SDS 聚丙烯酰胺凝胶电泳，这两种酶都是同源二聚体，亚单位分子量分别为 29 kDa 和 30 kDa。STKER-II 和 -III 在 pH 7.0 到 10.0 及 pH 5.5 到 9.0 的范围内都表现出稳定性。乙基 3-甲基-2-氧代丁酸酯被两种分离的酶还原为相应的 (R)-氢氧基酯，且具有优异的对映体过量。STKER-III 对体积较大的底物的还原具有较高的立体选择性，而 STKER-II 催化的还原选择性较低，除了乙基 3-甲基-2-羟基丁酸酯。两种酶对具有长烷基链的脂肪族酮酯的 Km 值较小。
• Stereoselective Reduction of Carbonyl Compounds with Actinomycete: Purification and Characterization of Three α-Keto Ester Reductases from<i>Streptomyces avermitilis</i>
  作者：Kohji ISHIHARA、Chiaki KATO、Hitomi YAMAGUCHI、Rieko IWAI、Momoko YOSHIDA、Natsumi IKEDA、Hiroki HAMADA、Noriyoshi MASUOKA、Nobuyoshi NAKAJIMA

  DOI：10.1271/bbb.80537

  日期：2008.12.23

  We achieved the purification of three alpha-keto ester reductases (Streptomyces avermitilis keto ester reductase, SAKERs-I, -II, and -III) from Streptomyces avermitilis NBRC14893 whole cells. The molecular masses of the native SAKERs-I, -II, and -III were estimated to be 72, 38, and 36 kDa, respectively, by gel filtration chromatography. The subunit molecular masses of SAKERs-I, -II, and -III were

  我们实现了从阿维链霉菌NBRC14893全细胞中纯化三种α-酮基酯还原酶（阿维链霉菌酮酯还原酶，SAKERs-I，-II和-III）。通过凝胶过滤色谱法，天然SAKERs-I，-II和-III的分子量分别估计为72、38和36kDa。通过SDS-聚丙烯酰胺凝胶电泳，SAKERs-I，-II和-III的亚基分子量也分别估计为32、32和34 kDa。纯化的SAKERs-II和-III对α-酮酸酯（特别是丙酮酸乙酯）具有还原活性。SAKER-1不仅对α-和β-酮酯具有高还原活性，而且对α-酮酸也具有高还原活性。SAKERs-I，-II，的N端氨基酸序列
• Stereoselective Reduction of Carbonyl Compounds Using the Cell-Free Extract of the Earthworm,<i>Lumbricus rubellus</i>, as a Novel Source of Biocatalyst
  作者：Kohji ISHIHARA、Nobuyoshi NAKAJIMA

  DOI：10.1271/bbb.60408

  日期：2006.12.23

  We found the reducing activity toward carbonyl compounds in the cell-free extract of the earthworm, Lumbricus rubellus. The earthworm extract had a reducing activity for keto esters in the presence of NADH or NADPH as a coenzyme. The earthworm extract reduced ethyl 3-methyl-2-oxobutanoate to the corresponding alcohol with a high enantiomeric excess (91%, R-form) at 50 °C in the presence of NADH. In particular, ethyl 2-oxoheptanoate was exclusively reduced to the corresponding (R)-hydroxyl ester with a high enantiomeric excess (>99%).

  我们发现，在蚯蚓（Lumbricus rubellus）的无细胞提取物中对羰基化合物具有还原活性。在NADH或NADPH作为辅酶的存在下，蚯蚓提取物对酮酯表现出还原活性。在50°C下，蚯蚓提取物在NADH的存在下，将乙基3-甲基-2-氧代丁酸酯还原为相应的醇，并具有高的对映体过量（91%，R型）。特别地，乙基2-氧代庚酸酯被独占性地还原为相应的（R）-羟基酯，且对映体过量超过99%。