(S)-1-methylpropyl propanoate | 474021-89-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-1-methylpropyl propanoate
• 英文别名: [(2S)-butan-2-yl] propanoate
• CAS: 474021-89-1
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: VPSLGSSVPWVZFG-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-(+)-2-丁醇 、 丙酸甲酯 在 Novozym 435 作用下， 以 叔丁醇 为溶剂， 生成 (S)-1-methylpropyl propanoate
  参考文献：
  名称：

  Contribution of both catalytic constant and Michaelis constant to CALB enantioselectivity: Use of FEP calculations for prediction studies

  摘要：

  Candida antarctica lipase B (CALB) is characterized by its stability and ease of production and is widely used in the pharmaceutical industry. Here we report on the enantioselectivity of the enzyme using both experimental and computational methods. The apparent kinetic parameters were first experimentally determined for enantiopure butan-2-ol and pentan-2-ol substrates. We demonstrate that enantio-preference for the R form of butan-2-ol arises mainly from a lower apparent K-M. This corresponds to a major contribution of Delta Delta G(ES), the free energy difference between the ES complex formed with the R and S enantiomers, to Delta Delta G(t), the free energy difference between both transit ion states, in comparison with Delta Delta G(kcat), the activation free energy difference. In the case of pentan-2-ol, we show that the enantiopreference for the R form conies from both a lower K-M and a higher k(cat). In addition, we used, for the first time, the free energy perturbation method to evaluate the free energy difference between tetrahedral intermediates formed with R and S alcohol enantiomers for a series of secondary alcohols. This is a valid model for Delta Delta G(t). Computational results were found to be in qualitative agreement with experimental data, and enable the determination of substrate orientation in the active site with fair confidence. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.11.020

文献信息

• Structural basis for a highly (S)-enantioselective reductase towards aliphatic ketones with only one carbon difference between side chain
  作者：Afifa Ayu Koesoema、Yosuke Sugiyama、Zichang Xu、Daron M. Standley、Miki Senda、Toshiya Senda、Tomoko Matsuda

  DOI：10.1007/s00253-019-10093-w

  日期：2019.12

  Aliphatic ketones, such as 2-butanone and 3-hexanone, with only one carbon difference among side chains adjacent to the carbonyl carbon are difficult to be reduced enantioselectively. In this study, we utilized an acetophenone reductase from Geotrichum candidum NBRC 4597 (GcAPRD) to reduce challenging aliphatic ketones such as 2-butanone (methyl ethyl ketone) and 3-hexanone (ethyl propyl ketone) to their

  在与羰基碳相邻的侧链中仅具有一个碳差异的2-酮丁酮和3-己酮等脂肪族酮难以对映选择性地还原。在这项研究中，我们利用了来自Geotrichum candidum NBRC 4597（GcAPRD）的苯乙酮还原酶将具有挑战性的脂族酮（例如2-丁酮（甲乙酮）和3-己酮（乙丙酮））还原为相应的（S）醇， ee分别为94％ee和> 99％ee。通过晶体结构的确定，表明残基Trp288限制了小的结合口袋的大小。对接模拟表明，Trp288在形成CH⋯π相互作用方面起着重要的作用，以使pro-S结合态中的酮正确定向，从而生成（S）醇。
• Catechol protected levodopa diester prodrugs, compositions, and methods of use
  申请人：Xiang Jia-Ning

  公开号：US20080171789A1

  公开（公告）日：2008-07-17

  Catechol protected levodopa diester prodrugs pharmaceutical, compositions comprising catechol protected levodopa diester prodrugs, and methods of using such prodrugs and pharmaceutical compositions for treating diseases such as Parkinson's disease are provided.

  提供了一种保护左旋多巴二酯前药的制药品，包括含有保护左旋多巴二酯前药的制剂，以及利用这种前药和制药组合物治疗帕金森病等疾病的方法。
• Levodopa dimethyl-substituted diester prodrugs compositions, and methods of use
  申请人：Xiang Jia-Ning

  公开号：US20080214663A1

  公开（公告）日：2008-09-04

  Levodopa dimethyl-substituted diester prodrugs pharmaceutical, compositions comprising levodopa dimethyl-substituted diester prodrugs, and methods of using such prodrugs and pharmaceutical compositions for treating diseases such as Parkinson's disease are provided.

  本文提供了左旋多巴二甲基取代二酯前药制剂、包含左旋多巴二甲基取代二酯前药制剂的药物组合物，以及使用这些前药和药物组合物治疗帕金森病等疾病的方法。
• LEVODOPA DIMETHYL-SUBSTITUTED DIESTER PRODRUGS, COMPOSITIONS, AND METHODS OF USE
  申请人：Xiang Jia-Ning

  公开号：US20100173992A1

  公开（公告）日：2010-07-08

  Levodopa dimethyl-substituted diester prodrugs pharmaceutical, compositions comprising levodopa dimethyl-substituted diester prodrugs, and methods of using such prodrugs and pharmaceutical compositions for treating diseases such as Parkinson's disease are provided.

  本发明提供了左旋多巴二甲基取代二酯前药制剂、包含左旋多巴二甲基取代二酯前药制剂的制剂组合物，以及使用这些前药制剂和制剂组合物治疗帕金森病等疾病的方法。
• METHODS AND MATERIALS FOR MAKING SIMVASTATIN AND RELATED COMPOUNDS
  申请人：The Regents of the University of California

  公开号：US20150203884A1

  公开（公告）日：2015-07-23

  The invention disclosed herein relates to methods and materials for producing simvastatin and related compounds such as huvastatin.