(S)-2-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentanedioic acid 5-methyl ester | 721944-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: (S)-2-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentanedioic acid 5-methyl ester
• CAS: 721944-05-4
• 化学式: C₁₆H₂₅N₃O₆S
• 分子量: 387.457
• InChiKey: AMYOWQWQZIQGGB-RMIALFOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.23
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  133.83
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentanedioic acid 5-methyl ester 在 TEA 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  Enzyme cleavable and biotinylated photoaffinity ligand with diazirine

  摘要：

  The efficient synthesis of an enzyme cleavable biotinylated diazirinyl photoaffinity ligand is described to allow the effective manipulation of the photolabeled biocomponents. The compound contains a glutamic acid gamma-methyl ester, which is a precursor of the substrate for V8 protease, between the diazirinyl photophor and biotin moiety. After alkaline hydrolysis of the ester, the compound can be proteolyzed at the Glu moiety by V8 protease. The photophore was introduced to L-Phe p-nitroanilide and the ligand was applied to photolabel of chymotrypsin to manipulate the application of the concept. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.011
• 作为产物：
  描述：

  L-谷氨酸-5-甲酯 、 (+)生物素-N-琥珀酰亚胺基酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以81%的产率得到(S)-2-[5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentanedioic acid 5-methyl ester
  参考文献：
  名称：

  Enzyme cleavable and biotinylated photoaffinity ligand with diazirine

  摘要：

  The efficient synthesis of an enzyme cleavable biotinylated diazirinyl photoaffinity ligand is described to allow the effective manipulation of the photolabeled biocomponents. The compound contains a glutamic acid gamma-methyl ester, which is a precursor of the substrate for V8 protease, between the diazirinyl photophor and biotin moiety. After alkaline hydrolysis of the ester, the compound can be proteolyzed at the Glu moiety by V8 protease. The photophore was introduced to L-Phe p-nitroanilide and the ligand was applied to photolabel of chymotrypsin to manipulate the application of the concept. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.011