(R)-3-氨基-5-甲基己酸 | 91298-67-8

• 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
• 中文名称: (R)-3-氨基-5-甲基己酸
• 英文名称: (R)-3-amino-5-methylhexanoic acid
• 英文别名: 3-amino-5-methylhexanoic acid；D-β-homoleucine；β-homoleucine；(R)-3-Amino-5-methyl-hexanoic acid；(3R)-3-amino-5-methylhexanoic acid
• CAS: 91298-67-8
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: MLYMSIKVLAPCAK-ZCFIWIBFSA-N

物化性质

• 沸点：
  249.1±23.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922499990
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-氯-2-氟硝基苯 、 (R)-3-氨基-5-甲基己酸 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成
  参考文献：
  名称：

  Fragment-based discovery and optimization of BACE1 inhibitors

  摘要：

  A novel series of 2-aminobenzimidazole inhibitors of BACE1 has been discovered using fragment-based drug discovery (FBDD) techniques. The rapid optimization of these inhibitors using structure-guided medicinal chemistry is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.089
• 作为产物：
  描述：

  2-甲基-2-丙基(2E)-5-甲基-2-己烯酸酯 在 palladium dihydroxide 正丁基锂 、 氢气 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 42.5h， 生成 (R)-3-氨基-5-甲基己酸
  参考文献：
  名称：

  平行合成手性β-氨基酸

  摘要：

  使用高手性锂N-苄基-N-（α-甲基苄基）酰胺的共轭加成，完成了对映体纯度高的30个β-氨基酸阵列的平行不对称合成。该协议的实验简单性和高度实用性通过高15种α，β-不饱和酯的高效平行转化为相应β-氨基酸的对映体系列以高总收率和选择性进行了证明，且每个步骤的纯化步骤最少反应方案。

  DOI：

  10.1016/j.tetasy.2007.06.008

文献信息

• Synthesis of Enantiomerically Pure β- and γ-Amino Acids from Aspartic and Glutamic Acid Derivatives
  作者：A. El Marini、M. L. Roumestant、Ph. Viallefont、D. Razafindramboa、M. Bonato、M. Follet

  DOI：10.1055/s-1992-26315

  日期：——

  An efficient synthesis of enantiomerically pure β- and γ-amino acids starting from commercially available aspartic and glutamic acid derivatives is described. The acid function, α to the amino group, is first transformed to a good leaving group and the product reacted with organocuprates to yield β-and γ-amino esters. After deprotection β- and γ-amino acids are obtained in good overall yields.

  描述了一种高效合成手性纯的β-和γ-氨基酸的方法，该方法从市售的谷氨酸和天冬氨酸衍生物出发。首先将氨基酸的α位羧基转化为良好的离去基团，然后与有机铜试剂反应，生成β-和γ-氨基酸酯。经过脱保护步骤后，以良好的总产率获得β-和γ-氨基酸。
• Conformational stability studies of a stapled hexa-β3-peptide library
  作者：Romila D. Gopalan、Mark P. Del Borgo、Ylva E. Bergman、Sharon Unabia、Roger J. Mulder、Matthew C. J. Wilce、Jacqueline A. Wilce、Marie-Isabel Aguilar、Patrick Perlmutter

  DOI：10.1039/c2ob06617c

  日期：——

  A library of 14-helical hexa β3-peptides was synthesized in order to determine the influence of sequence variation as well as staple size and location on conformational stability. From this study we show that appropriately stapled hexa-β3-peptides can allow for a number of variations without significant perturbation of the 14-helix.

  为了确定序列变化以及主链大小和位置对构象稳定性的影响，我们合成了14螺旋六β3肽库。通过这项研究，我们发现，适当连接的六β3肽可以允许一些变化，而不会显著干扰14螺旋。
• N-Acetyl-(R,S)-beta-Amino Acid Acylase Gene
  申请人：Suzuki Shunichi

  公开号：US20080241895A1

  公开（公告）日：2008-10-02

  The present invention provides genes that encode the N-acetyl-(R,S)-β-amino acid acylases. The N-acetyl-(R,S)-β-amino acid acylases were isolated and purified from bacterial cells and the nucleotide sequences were determined. A host, such as Escherichia coli , was used to construct a high-expression system for these genes. The N-acetyl-(R)-β-amino acid acylase produced by Burkholderia sp. AJ110349 (FERM BP-10366) includes, for example, the protein having the amino acid sequence shown in SEQ. ID. NO. 8. The gene encoding this enzyme includes, for example, the DNA having the nucleotide sequence as shown in SEQ. ID. NO. 7. The N-acetyl-(S)-β-amino acid acylase produced by Burkholderia sp. AJ110349 (FERM BP-10366) includes, for example, the protein having the amino acid sequence shown in SEQ. ID. NO. 10. The gene encoding this enzyme includes, for example, the DNA having the nucleotide sequence shown inshown in SEQ. ID. NO. 9. The N-acetyl-(R)-β-amino acid acylase produced by Variovorax sp. AJ110348 (FERM BP-10367) includes, for example, the protein comprised of the amino acid sequence shown in SEQ. ID. NO. 12. The gene encoding this enzyme includes, for example, the DNA having the nucleotide sequence shown inshown in SEQ. ID. NO. 11.

  本发明提供了编码N-乙酰-(R,S)-β-氨基酸酰化酶的基因。N-乙酰-(R,S)-β-氨基酸酰化酶从细菌细胞中分离和纯化，并确定了核苷酸序列。宿主，例如大肠杆菌，被用于构建这些基因的高表达系统。Burkholderia sp. AJ110349 (FERM BP-10366)产生的N-乙酰-(R)-β-氨基酸酰化酶，例如包括具有SEQ. ID. NO. 8所示的氨基酸序列的蛋白质。编码这种酶的基因，例如包括具有SEQ. ID. NO. 7所示的核苷酸序列的DNA。Burkholderia sp. AJ110349 (FERM BP-10366)产生的N-乙酰-(S)-β-氨基酸酰化酶，例如包括具有SEQ. ID. NO. 10所示的氨基酸序列的蛋白质。编码这种酶的基因，例如包括具有SEQ. ID. NO. 9所示的核苷酸序列的DNA。Variovorax sp. AJ110348 (FERM BP-10367)产生的N-乙酰-(R)-β-氨基酸酰化酶，例如包括由SEQ. ID. NO. 12所示的氨基酸序列组成的蛋白质。编码这种酶的基因，例如包括具有SEQ. ID. NO. 11所示的核苷酸序列的DNA。
• Asymmetric reductive amination of keto acid derivatives for producing amino acid derivatives
  申请人：Matsumura Kazuhiko

  公开号：US20070142443A1

  公开（公告）日：2007-06-21

  The present invention relates to a process for producing amino acid derivatives such as optically active β-amino acid in short steps with good yield and high optical purity, which comprises reacting a keto acid of the formula (1): wherein R 1 is hydrogen, an optionally substituted hydrocarbon, etc.; R 2 is a spacer; and R 3 is an optionally substituted alkoxy, etc., or a salt thereof, with ammonia or an amine or a salt thereof in the presence of a chiral catalyst and in the presence or absence of an acid and/or a fluorine-containing alcohol, to give an amino acid derivative of the formula (2): wherein Q is a group formed by removing one hydrogen atom from ammonia or an amine; X′ is an acid and/or a fluorine-containing alcohol; and b is 0 or 1.

  本发明涉及一种生产氨基酸衍生物的方法，例如短步骤中产生具有良好收率和高光学纯度的光学活性β-氨基酸。该方法包括在手性催化剂的存在下，与氨或胺或其盐一起在酸和/或含氟醇的存在或缺席下反应式（1）的酮酸： 其中，R1是氢、可选取代的碳氢化合物等；R2是间隔物；R3是可选取代的烷氧基等，或其盐，以得到式（2）的氨基酸衍生物： 其中，Q是从氨或胺中去除一个氢原子形成的基团；X'是酸和/或含氟醇；b为0或1。
• Cyclin Based Inhibitors of CDK2 and CDK4
  申请人：University of South Carolina

  公开号：US20150011730A1

  公开（公告）日：2015-01-08

  Structural and functional analysis of peptide inhibitor binding to the cyclin D and cyclin A groove has been investigated and used to design peptides that provide the basis for structure-activity relationships, have improved binding and have potential for development as chemical biology probes, as potential diagnostics and as therapeutics in the treatment of proliferative diseases including cancer and inflammation.

  对肽抑制剂与细胞周期素D和细胞周期素A凹槽的结构和功能分析已经进行了研究，并用于设计肽，为结构活性关系提供基础，具有改善结合能力并具有潜力作为化学生物学探针，潜在诊断工具和治疗增生性疾病，包括癌症和炎症。