methyl bis-(cyanoethyl)glycinate | 891846-45-0

• 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: methyl bis-(cyanoethyl)glycinate
• 英文别名: Methyl 2-amino-4-cyano-2-(2-cyanoethyl)butanoate；methyl 2-amino-4-cyano-2-(2-cyanoethyl)butanoate
• CAS: 891846-45-0
• 化学式: C₉H₁₃N₃O₂
• 分子量: 195.221
• InChiKey: IDZJLTYNFBUCGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  99.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl bis-(cyanoethyl)glycinate 在 镍 N-甲基吗啉 、 sodium hydroxide 、 氢气 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 12.0h， 生成 5-Allyloxycarbonylamino-2-(3-allyloxycarbonylamino-propyl)-2-(3-tert-butoxycarbonylamino-propionylamino)-pentanoic acid
  参考文献：
  名称：

  ‘Bis-ornithine’ (2,2-bis(aminopropyl)glycine): a new tetravalent template for assembling different functional peptides

  摘要：

  Synthesis of bis-ornithine. a new C-alpha,C-alpha-disubstituted alpha-amino acid bearing orthogonally protected alpha and delta amine groups is reported. Bis-ornithine (bisOrn) and dipeptides containing bis-ornithine have been synthesized in solution up to multigram scale. As a first example, one of these compounds Boc-beta Ala-bisOrn(Alloc)(2)-OH has been attached to a solid support and used as template for the synthesis of a symmetrical assemblage of peptides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.136
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 methyl bis-(cyanoethyl)glycinate
  参考文献：
  名称：

  ‘Bis-ornithine’ (2,2-bis(aminopropyl)glycine): a new tetravalent template for assembling different functional peptides

  摘要：

  Synthesis of bis-ornithine. a new C-alpha,C-alpha-disubstituted alpha-amino acid bearing orthogonally protected alpha and delta amine groups is reported. Bis-ornithine (bisOrn) and dipeptides containing bis-ornithine have been synthesized in solution up to multigram scale. As a first example, one of these compounds Boc-beta Ala-bisOrn(Alloc)(2)-OH has been attached to a solid support and used as template for the synthesis of a symmetrical assemblage of peptides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.136

文献信息

• Design, Synthesis, and Biological Studies of Efficient Multivalent Melanotropin Ligands: Tools toward Melanoma Diagnosis and Treatment
  作者：Nabila Brabez、Ronald M. Lynch、Liping Xu、Robert J. Gillies、Gerard Chassaing、Solange Lavielle、Victor J. Hruby

  DOI：10.1021/jm2009937

  日期：2011.10.27

  To achieve early detection and specific cancer treatment, we propose the use of multivalent interactions in which a series of binding events leads to increased affinity and consequently to selectivity. Using melanotropin (MSH) ligands, our aim is to target melanoma cells which overexpress melanocortin receptors. In this study, we report the design and efficient synthesis of new trivalent ligands bearing MSH ligands. Evaluation of these multimers on a cell model engineered to overexpress melanocortin 4 receptors (MC4R) showed up to a 350-fold increase in binding compared to the monomer, resulting in a trivalent construct with nanomolar affinity starting from a micromolar affinity ligand. Cyclic adenosine monophosphate (cAMP) production was also investigated, leading to more insights into the effects of multivalent compounds on transduction mechanisms.
• ‘Bis-ornithine’ (2,2-bis(aminopropyl)glycine): a new tetravalent template for assembling different functional peptides
  作者：Baptiste Aussedat、Gérard Chassaing、Solange Lavielle、Fabienne Burlina

  DOI：10.1016/j.tetlet.2006.03.136

  日期：2006.5

  Synthesis of bis-ornithine. a new C-alpha,C-alpha-disubstituted alpha-amino acid bearing orthogonally protected alpha and delta amine groups is reported. Bis-ornithine (bisOrn) and dipeptides containing bis-ornithine have been synthesized in solution up to multigram scale. As a first example, one of these compounds Boc-beta Ala-bisOrn(Alloc)(2)-OH has been attached to a solid support and used as template for the synthesis of a symmetrical assemblage of peptides. (c) 2006 Elsevier Ltd. All rights reserved.