benzyl 2-methyl-3-hydroxybutanoate

• 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: benzyl 2-methyl-3-hydroxybutanoate
• 英文别名: benzyl (2R,3S)-3-hydroxy-2-methylbutanoate
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: VDARBCCMTDKLBW-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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)-methoxytrifluoromethylphenylacetyl chloride 、 benzyl 2-methyl-3-hydroxybutanoate 在 吡啶 作用下， 反应 17.0h， 以33%的产率得到(2R,3S)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-butyric acid benzyl ester
  参考文献：
  名称：

  Akita, Hiroyuki; Furuichi, Akiya; Koshiji, Hiroko, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 12, p. 4376 - 4383

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-3-氧代丁酸苄酯 在 phosphate buffer 、 Klebsiella pneumoniae IFO 3319 、 还原型辅酶II(NADPH)四钠盐 作用下， 以91%的产率得到benzyl 2-methyl-3-hydroxybutanoate
  参考文献：
  名称：

  肺炎克雷伯菌IF03319的2-甲基-3-氧代丁酸乙酯还原酶的纯化和表征。

  摘要：

  在肺炎克雷伯菌IFO 3319细胞中发现了一种催化2-甲基-3-氧代丁酸乙酯（1）还原为（2R，3S）3-羟基-2-甲基丁酸乙酯的酶。从细胞中分离出酶，并通过硫酸铵分级分离，离子交换色谱，亲和色谱和凝胶过滤纯化250倍。发现纯化的酶是分子量约为31,000，等电点为6.2的单体蛋白。它是NADPH依赖性的，在pH 7.0和45°C下具有最大的还原活性，在pH 10.0和45°C下具有最大的氧化活性。pH 7.0的Km值分别是2-甲基-3-氧代丁酸苄酯的5.6 mM（对于1）和12.5 mM。以2-氧代环烷烃羧酸酯和2-甲基-3-氧代丁酸的酯为底物，

  DOI：

  10.1271/bbb.60.760

文献信息

• Stereochemical Control in Microbial Reduction. 9. Diastereoselective Reduction of 2-Alkyl-3-oxobutanoate with Bakers’ Yeast
  作者：Kaoru Nakamura、Takehiko Miyai、Ashish Nagar、Shinzaburo Oka、Atsuyoshi Ohno

  DOI：10.1246/bcsj.62.1179

  日期：1989.4.15

  Bakers’ yeast reduces esters of 2-alkyl-3-oxobutanoic acid (CH3COCHRCO2R′; R=methyl, ethyl, propyl, propargyl, and allyl) into the corresponding (S)-hydroxy esters with exclusive stereoselectivity, while the configuration at the 2-position of the hydroxy esters is either S (anti) or R (syn) depending on the structure of the alkoxyl group in the carboalkoxyl moiety of the ester. Oftenly, the stereoselectivity

  面包师的酵母将 2-烷基-3-氧代丁酸（CH3COCHRCO2R'；R=甲基、乙基、丙基、炔丙基和烯丙基）的酯还原为相应的（S）-羟基酯，具有独特的立体选择性，而在 2羟基酯的-位是S(反)或R(syn)，这取决于酯的碳烷氧基部分中烷氧基的结构。通常，关于 2 位的立体选择性并不令人满意。一般来说，叔丁酯的还原在产物中占主导地位，而 1,1-二甲基丙酯的还原则发挥顺式优势。从酯的合理构象的角度讨论了这两种酯在非对映选择性方面的显着差异。
• Access to Enantiopure α-Alkyl-β-hydroxy Esters through Dynamic Kinetic Resolutions Employing Purified/Overexpressed Alcohol Dehydrogenases
  作者：Aníbal Cuetos、Ana Rioz-Martínez、Fabricio R. Bisogno、Barbara Grischek、Iván Lavandera、Gonzalo de Gonzalo、Wolfgang Kroutil、Vicente Gotor

  DOI：10.1002/adsc.201200139

  日期：2012.6.18

  and Ralstonia sp. (RasADH) could also accept bulkier keto esters (‘bulky‐bulky’ substrates). SyADH also provided preferentially syn‐(2R,3S) isomers and RasADH showed in some cases good selectivity towards the formation of anti‐(2S,3S) derivatives. With anti‐Prelog ADHs such as LBADH from L. brevis or LKADH from L. kefir, syn‐(2S,3R) alcohols were obtained with high conversions and diastereomeric excess

  通过使用纯化或粗制的大肠杆菌过表达的醇脱氢酶（ADHs）的动态动力学拆分（DKR）获得α-烷基-β-羟基酯。ADH-A从R.曲霉，CPADH从近平滑念珠菌从和TesADH T. ethanolicus得到顺式- （2- [R，3小号）具有非常高的选择性为空间位不受阻碍酮（“小体积大的”底物）的衍生物，而的ADH来自S. yanoikuyae（SyADH）和Ralstonia sp。（RasADH）也可以接受更大的酮酯（“大块状”底物）。SyADH还提供了优先顺式- （2- ř，3 S）异构体和RasADH在某些情况下显示出对形成抗-（2 S，3 S）衍生物的良好选择性。与抗作为LBADH这样普雷洛格的ADH从短乳杆菌或从LKADH克菲尔乳杆菌，顺式- （2-小号，3 - [R ）与高转化率和对映体过量在某些情况下，特别是与LBADH得到醇。此外，由于这些底物在热力学上有利于还原，因此可以仅
• NAKAMURA, KAORU;MIYAI, TAKEHIKO;NAGAR, ASHISH;OKA, SHINZABURO;OHNO, ATSUY+, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 1179-1187
  作者：NAKAMURA, KAORU、MIYAI, TAKEHIKO、NAGAR, ASHISH、OKA, SHINZABURO、OHNO, ATSUY+

  DOI：——

  日期：——
• Furuichi, Akiya; Akita, Hiroyuki; Matsukura, Hiroko (nee Koshiji), Agricultural and Biological Chemistry, 1985, vol. 49, # 9, p. 2563 - 2570
  作者：Furuichi, Akiya、Akita, Hiroyuki、Matsukura, Hiroko (nee Koshiji)、Oishi, Takeshi、Horikoshi, Koki

  DOI：——

  日期：——
• Probe Compound for Detecting and Isolating Enzymes and Means and Methods Using the Same
  申请人：Golyshin Peter N.

  公开号：US20120231972A1

  公开（公告）日：2012-09-13

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.