(S)-2-amino-8-bromooctanoic acid

• 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)-2-amino-8-bromooctanoic acid
• 英文别名: (2S)-2-amino-8-bromooctanoic acid
• 化学式: C₈H₁₆BrNO₂
• 分子量: 238.125
• InChiKey: JJDAGLZUYFOZLM-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (S)-2-amino-8-bromooctanoic acid 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 、 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 10.0h， 生成 tert-butyl (2S)-8-acetylsulfanyl-2-(phenylmethoxycarbonylamino)octanoate
  参考文献：
  名称：

  A novel series of l-2-benzyloxycarbonylamino-8-(2-pyridyl)-disulfidyloctanoic acid derivatives as histone deacetylase inhibitors: Design, synthesis and molecular modeling study

  摘要：

  Histone deacetylases inhibitors (HDACIs) have become an attractive class of anticancer agents. In order to find some novel potent HDACIs, we designed and synthesized a series of L-2-benzyloxycarbonylamino-8-(2-pyridyl)-disulfidyloctanoic acid derivatives. All compounds exhibited potent HDAC-inhibitory activity, and two of them had similar potency to TSA. The introduction of 2-amino-4-phenylthiazole or 9-methyleneoxy-fluorenyl group at the surface recognize domain of these HDACIs could greatly increase their HDAC-inhibitory activity. Molecular modeling studies indicated that coordination of the zinc ion by these inhibitors, and formation of hydrogen bond and hydrophobic interaction between inhibitors and HDACs were essential for the HDAC-inhibitory activities of these inhibitors. Asp181, Asp269, Leu276 and Tyr308 in the active site of HDAC2 gave favorable contributions for binding with all compounds. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.009
• 作为产物：
  描述：

  diethyl acetamido(6-bromohexyl)malonate 在 sodium hydroxide 、 Aspergillus genus aminoacylase 、 cobalt(II) chloride 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 41.0h， 生成 (S)-2-amino-8-bromooctanoic acid
  参考文献：
  名称：

  用于侧链修饰的1-α-氨基-ω-溴链烷酸的合成

  摘要：

  侧链长度在4至10个亚甲基单元之间变化的1-α-氨基-ω-溴链烷酸已经方便地合成为有用的中间体，用于合成官能化的非天然氨基酸。

  DOI：

  10.1016/j.tetlet.2003.11.007

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％。
• 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。
• OPTICALLY ACTIVE ALPHA-AMINO ACID INTO WHICH BSH IS INTRODUCED AND METHOD FOR SYNTHESIZING THE SAME
  申请人：Kirihata Mitsunori

  公开号：US20110124914A1

  公开（公告）日：2011-05-26

  Disclosed is the method for producing an optically active BSH amino acid, which comprises a step of reacting an optically active a-amino acid derivative having a halogen in a side chain with a cyanoethyl BSH compound represented by formula (1). An optically active BSH amino acid obtained by the method is also disclosed.

  本发明揭示了一种生产光学活性BSH氨基酸的方法，其中包括将侧链中带有卤素的光学活性a-氨基酸衍生物与由式（1）表示的氰乙基BSH化合物反应的步骤。本发明还揭示了通过该方法获得的光学活性BSH氨基酸。
• OPTICALLY ACTIVE alpha-AMINO ACID INTO WHICH BSH IS INTRODUCED AND METHOD FOR SYNTHESIZING THE SAME
  申请人：Stella Pharma Corporation

  公开号：EP2319850B1

  公开（公告）日：2017-03-29
• Inhibitors selective for HDAC6 in enzymes and cells
  作者：Praveer K. Gupta、Robert C. Reid、Ligong Liu、Andrew J. Lucke、Steve A. Broomfield、Melanie R. Andrews、Matthew J. Sweet、David P. Fairlie

  DOI：10.1016/j.bmcl.2010.09.100

  日期：2010.12

  Histone deacetylase inhibitors with anticancer or anti-inflammatory activity bind to Class I or Class I and II HDAC enzymes. Here we compare selectivity of inhibitors of a Class II HDAC enzyme (HDAC6) and find one that retains high selectivity in macrophages. (C) 2010 Elsevier Ltd. All rights reserved.