(2S)-5-叠氮基-2-甲基戊酸 | 499101-12-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (2S)-5-叠氮基-2-甲基戊酸
• 英文名称: (2S)-5-azido-2-methylvaleric acid
• 英文别名: (2S)-5-Azido-2-methylpentanoic acid；(2S)-5-azido-2-methylpentanoic acid
• CAS: 499101-12-1
• 化学式: C₆H₁₁N₃O₂
• 分子量: 157.172
• InChiKey: LCBQKSUSPAOOTE-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-5-叠氮基-2-甲基戊酸 在 六氟异丙醇 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 89.17h， 生成 (3S,6S,9S,12S)-3-benzyl-6-isobutyl-9,12-dimethyl-1,4,7,10-tetraza-2,5,8,11-cyclopentadecanetetrone
  参考文献：
  名称：

  Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- and C-Methylations Fine-Tune Conformation and Properties

  摘要：

  DOI：

  10.1021/acs.jmedchem.0c02036
• 作为产物：
  描述：

  5-叠氮基戊酸 在 lithium hydroxide 、 双氧水 、 三甲基乙酰氯 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 7.5h， 生成 (2S)-5-叠氮基-2-甲基戊酸
  参考文献：
  名称：

  Synthesis of Cα methylated carboxylic acids: isosteres of arginine and lysine for use as N-terminal capping residues in polypeptides

  摘要：

  Replacement of the N-terminal alpha-amine with the isosteric methyl functionality in bioactive peptides can influence various pharmacokinetic parameters, including hydrophobicity and stability. C-alpha methylated amino acid analogues are thus of great interest to expand the repertoire of nonnatural synthons available as N-terminal 'capping' residues for peptide-based drug design. Several novel arginine and lysine analogues stereo selectively modified in the C-alpha position with a methyl group in place of the alpha-amine were prepared. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.056

文献信息

• PEPTIDE-COMPOUND CYCLIZATION METHOD
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20150080549A1

  公开（公告）日：2015-03-19

  An object of the present invention is to provide methods of discovering drugs effective for tough targets, which have conventionally been discovered only with difficulty. The present invention relates to novel methods for cyclizing peptide compounds, and novel peptide compounds and libraries comprising the same, to achieve the above object.

  本发明的目的是提供一种发现对于难以处理的靶点有效的药物的方法，这些药物通常很难被发现。本发明涉及新型的环化肽化合物的方法，以及包含这些化合物的新型肽库，以实现上述目的。
• Effect of Conformational Preorganization of a Three-Armed Host on Anion Binding and Selectivity
  作者：Frank Hettche、Philipp Reiß、Reinhard W. Hoffmann

  DOI：10.1002/1521-3765(20021104)8:21<4946::aid-chem4946>3.0.co;2-v

  日期：2002.11.4

  A set of three-armed urea-containing anion receptors was prepared. The receptors all have the same binding topology but differ in the level of conformational preorganisation with respect to the arrangement of the side-arms relative to the platform and within the side arms themselves. This is mirrored in a specific increase (x 2.5) in the binding constant for chloride and in a 12-fold increase in the chloride nitrate-selectivity.
• US9409952B2
  申请人：——

  公开号：US9409952B2

  公开（公告）日：2016-08-09
• Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- and C-Methylations Fine-Tune Conformation and Properties
  作者：Christian Comeau、Benjamin Ries、Thomas Stadelmann、Jacob Tremblay、Sylvain Poulet、Ulrike Fröhlich、Jérôme Côté、Pierre-Luc Boudreault、Rabeb Mouna Derbali、Philippe Sarret、Michel Grandbois、Grégoire Leclair、Sereina Riniker、Éric Marsault

  DOI：10.1021/acs.jmedchem.0c02036

  日期：2021.5.13
• Synthesis of Cα methylated carboxylic acids: isosteres of arginine and lysine for use as N-terminal capping residues in polypeptides
  作者：Kevin S. Orwig、Thomas A. Dix

  DOI：10.1016/j.tetlet.2005.08.056

  日期：2005.10

  Replacement of the N-terminal alpha-amine with the isosteric methyl functionality in bioactive peptides can influence various pharmacokinetic parameters, including hydrophobicity and stability. C-alpha methylated amino acid analogues are thus of great interest to expand the repertoire of nonnatural synthons available as N-terminal 'capping' residues for peptide-based drug design. Several novel arginine and lysine analogues stereo selectively modified in the C-alpha position with a methyl group in place of the alpha-amine were prepared. (c) 2005 Elsevier Ltd. All rights reserved.