(2S)-2-Amino-4-ethylhexansaeure | 134055-71-3

• 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: (2S)-2-Amino-4-ethylhexansaeure
• 英文别名: (2S)-2-amino-4-ethylhexanoic acid
• CAS: 134055-71-3
• 化学式: C₈H₁₇NO₂
• 分子量: 159.228
• InChiKey: FNTZSUXNNTXOEI-ZETCQYMHSA-N

物化性质

• 熔点：
  220 °C (decomp)
• 沸点：
  260.9±23.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S)-2-Amino-4-ethylhexansaeure 在 氯化亚砜 作用下， 生成 Methyl 4-ethyl-L-norleucinate
  参考文献：
  名称：

  Chiral Pyridoxal-Catalyzed Asymmetric Biomimetic Transamination of α-Keto Acids

  摘要：

  A series of chiral pyridoxals 8 and 9 have been developed from commercially available pyridoxine and (S)-alpha,alpha-diarylprolinols. The pyridoxals exhibited good catalytic activity in an asymmetric transamination of alpha-keto acids with 2,2-diphenylglycine (7f) as the amine source to give various alpha-amino acids in 29-85% yields with 53-80% ee's. The current asymmetric transamination has successfully mimicked a complete biological transamination process characterized by two half-transaminations, a small chiral pyridoxal molecule acting as the catalyst, and enantioselective control.

  DOI：

  10.1021/acs.orglett.5b02895
• 作为产物：
  描述：

  在 盐酸 、 Dowex 50W 作用下， 以 甲苯 为溶剂， 以34%的产率得到(2S)-2-Amino-4-ethylhexansaeure
  参考文献：
  名称：

  Seebach, Dieter; Buerger, H. Michael; Schickli, Christof P., Liebigs Annalen der Chemie, 1991, # 7, p. 669 - 684

  摘要：

  DOI：

文献信息

• Enantioselective biomimetic transamination of α-keto acids catalyzed by H4-naphthalene-derived axially chiral biaryl pyridoxamines
  作者：Chengkang Hou、Guoqing Zhao、Dongfang Xu、Baoguo Zhao

  DOI：10.1016/j.tetlet.2018.01.089

  日期：2018.3

  Asymmetric biomimetic transamination is a highly attractive method for synthesis of chemically and biologically important chiral amino acids and chiral amines. Development of chiral pyridoxamines/pyridoxals is the key for the reaction. New axially chiral biaryl pyridoxamines based on H4-naphathene skeleton have been developed. The pyridoxamines display good enantioselectivity and high catalytic activity

  不对称仿生转氨反应是合成化学和生物学上重要的手性氨基酸和手性胺的极具吸引力的方法。手性吡ido胺/吡rid醛的开发是反应的关键。已经开发了基于H 4-萘基骨架的新的轴向手性联芳基吡ido胺。吡ido胺在α-酮酸的不对称仿生转氨反应中表现出良好的对映选择性和高催化活性，可提供多种旋光性非天然氨基酸，产率为61-98％，ee可达91％。
• Asymmetric Transamination of α-Keto Acids Catalyzed by Chiral Pyridoxamines
  作者：Xiaoyu Lan、Chuangan Tao、Xuliang Liu、Aina Zhang、Baoguo Zhao

  DOI：10.1021/acs.orglett.6b01714

  日期：2016.8.5

  novel chiral pyridoxamines 3a–g containing a side chain has been developed. The pyridoxamines displayed catalytic activity and promising enantioselectivity in biomimetic asymmetric transamination of α-keto acids, to give various α-amino acids in 47–90% yields with up to 87% ee’s under very mild conditions. An interesting effect of the side chain on enantioselectivity was observed in the reaction.

  已开发出一种新型的含有侧链的新型手性吡ido胺3a – g。吡ido胺在α-酮酸的仿生不对称转氨反应中显示出催化活性和有前途的对映选择性，在非常温和的条件下，以47-90％的产率提供了高达87％ee的各种α-氨基酸。在反应中观察到侧链对对映选择性的有趣作用。
• Enzyme-Inspired Axially Chiral Pyridoxamines Armed with a Cooperative Lateral Amine Chain for Enantioselective Biomimetic Transamination
  作者：Yong Ethan Liu、Zhaole Lu、Bo Li、Jiaxin Tian、Feng Liu、Junyu Zhao、Chengkang Hou、Yingkun Li、Lili Niu、Baoguo Zhao

  DOI：10.1021/jacs.6b03930

  日期：2016.8.31

  transamination is catalyzed by pyridoxal/pyridoxamine, and it involves remarkable cooperative catalysis of a Lys residue in the transaminase. Inspired by transaminases, we developed a class of axially chiral pyridoxamines 11 bearing a lateral amine arm. The pyridoxamines exhibited high catalytic activity and excellent enantioselectivity in asymmetric transamination of α-keto acids, to give various α-amino

  酶促转氨由吡哆醛/吡哆胺催化，它涉及转氨酶中赖氨酸残基的显着协同催化。受转氨酶的启发，我们开发了一类带有侧胺臂的轴向手性吡哆胺 11。吡哆胺在 α-酮酸的不对称转氨反应中表现出高催化活性和优异的对映选择性，以 67-99% 的产率得到各种 α-氨基酸，ee's 为 83-94%。侧胺臂可能参与协同催化，因为 Lys 残基在生物转氨作用中进行，并且在活性和对映选择性方面对转氨作用具有重要影响。
• Influenza virus neutralizing peptidomimetic compounds
  申请人：Janssen Vaccines & Prevention B.V.

  公开号：US10738083B2

  公开（公告）日：2020-08-11

  The present invention relates to novel peptidomimetic compounds that are capable of binding to and/or neutralizing influenza viruses, in particular influenza A viruses of phylogenetic group 1, and to pharmaceutical compositions comprising such compounds. The invention also relates to the use of the peptidomimetic compounds in the diagnosis, prophylaxis and/or treatment of influenza virus infections.

  本发明涉及能够结合和/或中和流感病毒（尤其是系统发育群1的甲型流感病毒）的新型拟肽化合物，以及包含此类化合物的药物组合物。本发明还涉及拟肽化合物在诊断、预防和/或治疗流感病毒感染中的用途。
• INFLUENZA VIRUS NEUTRALIZING PEPTIDOMIMETIC COMPOUNDS
  申请人：Janssen Vaccines & Prevention B.V.

  公开号：EP3294753A1

  公开（公告）日：2018-03-21