(2S,3S)-3-amino-5-methylhexan-2-ol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3S)-3-amino-5-methylhexan-2-ol
• 化学式: C₇H₁₇NO
• 分子量: 131.218
• InChiKey: MGJSTMLRSUCUET-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  L-亮氨醇 在 草酰氯 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 7.0h， 生成 (2S,3S)-3-amino-5-methylhexan-2-ol
  参考文献：
  名称：

  Discovery of (S)-4-isobutyloxazolidin-2-one as a novel leucyl-tRNA synthetase (LRS)-targeted mTORC1 inhibitor

  摘要：

  A series of leucinol analogs were investigated as leucyl-tRNA synthetase-targeted mTORC1 inhibitors. Among them, compound 5, (S)-4-isobutyloxazolidin-2-one, showed the most potent inhibition on the mTORC1 pathway in a concentration-dependent manner. Compound 5 inhibited downstream phosphorylation of mTORC1 by blocking leucine-sensing ability of LRS, without affecting the catalytic activity of LRS. In addition, compound 5 exhibited cytotoxicity against rapamycin-resistant colon cancer cells, suggesting that LRS has the potential to serve as a novel therapeutic target. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.05.011

文献信息

• Pyridoxal-Catalyzed Racemization of α-Aminoketones Enables the Stereodivergent Synthesis of 1,2-Amino Alcohols Using Ketoreductases
  作者：Jingzhe Cao、Todd K. Hyster

  DOI：10.1021/acscatal.0c01502

  日期：2020.6.5

  variety of pharmaceutical and agrochemical molecules. Dynamic kinetic resolutions (DKRs) that involve the asymmetric reduction of α-amino ketones are attractive for preparing this motif; however, methods for racemizing the stereogenic α-carbon under mild conditions are underdeveloped. Here we report a chemoenzymatic DKR involving ketoreductases (KREDs), in which pyridoxal-5-phosphate (PLP) is used

  差异取代的1,2-氨基醇是各种药物和农业化学分子中的普遍基序。涉及不对称还原α-氨基酮的动态动力学拆分（DKR）对于制备该基序很有吸引力。然而，在温和条件下外消旋立构α-碳的方法尚不完善。在这里，我们报告涉及酮还原酶（KRED）的化学酶DKR，其中5-磷酸吡ido醛（PLP）用于催化外消旋α-氨基酮的外消旋化。该策略使得能够获得各种具有高非对映选择性和对映选择性的1,2-氨基醇。使用市售的KRED，可以访问所有四种可能的立体异构体，这突出说明了此方法的好处。
• Discovery of (S)-4-isobutyloxazolidin-2-one as a novel leucyl-tRNA synthetase (LRS)-targeted mTORC1 inhibitor
  作者：Suyoung Yoon、Jong Hyun Kim、Ina Yoon、Changhoon Kim、Sung-Eun Kim、Yura Koh、Seung Jae Jeong、Jiyoun Lee、Sunghoon Kim、Jeewoo Lee

  DOI：10.1016/j.bmcl.2016.05.011

  日期：2016.7

  A series of leucinol analogs were investigated as leucyl-tRNA synthetase-targeted mTORC1 inhibitors. Among them, compound 5, (S)-4-isobutyloxazolidin-2-one, showed the most potent inhibition on the mTORC1 pathway in a concentration-dependent manner. Compound 5 inhibited downstream phosphorylation of mTORC1 by blocking leucine-sensing ability of LRS, without affecting the catalytic activity of LRS. In addition, compound 5 exhibited cytotoxicity against rapamycin-resistant colon cancer cells, suggesting that LRS has the potential to serve as a novel therapeutic target. (C) 2016 Elsevier Ltd. All rights reserved.