(5S)-5-aminohexanoic acid | 1599-32-2

• 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: (5S)-5-aminohexanoic acid
• CAS: 1599-32-2
• 化学式: C₆H₁₃NO₂
• 分子量: 131.175
• InChiKey: IPCUHQYGWOKSLR-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (5S)-5-aminohexanoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 (S)-6-methylpiperidin-2-one
  参考文献：
  名称：

  通过工程胺脱氢酶立体选择性合成结构多样 (S)-内酰胺

  摘要：

  光学纯内酰胺具有广泛的应用，其中之一是作为合成农业生物活性化合物或药物的重要中间体。制造这些重要化学品需要在温和条件下用低成本胺供体高效立体选择性合成手性内酰胺。在此，设计了一种两步化学酶促策略，通过改造来自Thermoanaerobacter thermohydrosulfuricus ( Tther AmDH)的天然胺脱氢酶来生产 ( S )-内酰胺。其他AmDH 经过八个定向进化循环，以增强其对酮酸底物的还原胺化活性。这些变体对 6 种测试底物显示出更高的比活性，并在 γ- 和 δ- 内酰胺的不对称合成中提供高达 99% 的高立体选择性。特别是，Tther AmDH V8对模型底物乙酰丙酸表现出高 237 倍的比活性，并产生 99% ee的 ( S )-5-甲基-2-吡咯烷酮，时空产率为 75.3 g L -1  d -1。这些结果表明，工程化的胺脱氢酶Tther AmDH 可以作为

  DOI：

  10.1002/adsc.202200891
• 作为产物：
  描述：

  在 chromium(VI) oxide 、 硫酸 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 48.75h， 生成 (5S)-5-aminohexanoic acid
  参考文献：
  名称：

  (E)-Alkene and Ethylene Isosteres Substantially Alter the Hydrogen-Bonding Network in Class II MHC A^q/Glycopeptide Complexes and Affect T-Cell Recognition

  摘要：

  The structural basis for antigen presentation by class II major histocompatibility complex (MHC) proteins to CD4(+) T-cells is important for understanding and possibly treating autoimmune diseases. In the work described in this paper, (E)-alkene and ethylene amide-bond isosteres were used to investigate the effect of removing hydrogen-bonding possibilities from the CII259-270 glycopeptide, which is bound by the arthritis-associated murine A(q) class II MHC protein. The isostere-modified glycopeptides showed varying and unexpectedly large losses of A(q) binding that could be linked to the dynamics of the system. Molecular dynamics (MD) simulations revealed that the backbone of CII259-270 and the A(q) protein are able to form up to 11 hydrogen bonds, but fewer than this number are present at any one time. Most of the strong hydrogen-bond interactions were formed by the N-terminal part of the glycopeptide, i.e., in the region where the isosteric replacements were made. The structural dynamics also revealed that hydrogen bonds were strongly coupled to each other; the loss of one hydrogen-bond interaction had a profound effect on the entire hydrogen-bonding network. The A(q) binding data revealed that an ethylene isostere glycopeptide unexpectedly bound more strongly to A(q) than the corresponding (E)-alkene, which is in contrast to the trend observed for the other isosteres. Analysis of the MD trajectories revealed that the complex conformation of this ethylene isostere was structurally different and had an altered molecular interaction pattern compared to the other A(q)/glycopeptide complexes. The introduced amide-bond isosteres also affected the interactions of the glycopeptide/A(q) complexes with T-cell receptors. The dynamic variation of the patterns and strengths of the hydrogen-bond interactions in the class II MHC system is of critical importance for the class II MHC/peptide/TCR signaling system.

  DOI：

  10.1021/ja2038722

文献信息

• Bacteria engineered to treat diseases associated with hyperammonemia
  申请人：Synlogic Operating Company, Inc.

  公开号：US11060073B2

  公开（公告）日：2021-07-13

  Genetically engineered bacteria, pharmaceutical compositions thereof, and methods of modulating and treating disorders associated with hyperammonemia are disclosed.

  本研究公开了基因工程细菌、其药物组合物以及调节和治疗与高氨血症相关疾病的方法。
• BACTERIA ENGINEERED TO TREAT DISEASES ASSOCIATED WITH HYPERAMMONEMIA
  申请人：Synlogic, Inc.

  公开号：EP3307879A2

  公开（公告）日：2018-04-18
• Bacteria Engineered to Treat Diseases Associated with Hyperammonemia
  申请人：Synlogic, Inc.

  公开号：US20160333326A1

  公开（公告）日：2016-11-17

  Genetically engineered bacteria, pharmaceutical compositions thereof, and methods of modulating and treating disorders associated with hyperammonemia are disclosed.
• US9688967B2
  申请人：——

  公开号：US9688967B2

  公开（公告）日：2017-06-27
• [EN] BACTERIA ENGINEERED TO TREAT DISEASES ASSOCIATED WITH HYPERAMMONEMIA<br/>[FR] BACTÉRIES MODIFIÉES EN VUE DU TRAITEMENT DE MALADIES ASSOCIÉES À L'HYPERAMMONIÉMIE
  申请人：SYNLOGIC INC

  公开号：WO2016200614A2

  公开（公告）日：2016-12-15

  Genetically engineered bacteria, pharmaceutical compositions thereof, and methods of modulating and treating disorders associated with hyperammonemia are disclosed.