1',3'-dimethyl biotin | 99147-44-1

• 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: 1',3'-dimethyl biotin
• 英文别名: 5-((3aS)-1,3-dimethyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid；1,3-Dimethyl-biotin；N,N'-dimethyl-biotin；5-[(3as,4s,6ar)-1,3-Dimethyl-2-Oxohexahydro-1h-Thieno[3,4-D]imidazol-4-Yl]pentanoic Acid；5-[(3aS,4S,6aR)-1,3-dimethyl-2-oxo-3a,4,6,6a-tetrahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid
• CAS: 99147-44-1
• 化学式: C₁₂H₂₀N₂O₃S
• 分子量: 272.368
• InChiKey: PECDAVNFXWSGFV-QXEWZRGKSA-N

物化性质

• 沸点：
  477.6±30.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  86.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((2-aminoethyl)carbamoyl)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid 、 1',3'-dimethyl biotin 在 4-二甲氨基吡啶 、 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以26%的产率得到
  参考文献：
  名称：

  Artificial Ligands of Streptavidin (ALiS): Discovery, Characterization, and Application for Reversible Control of Intracellular Protein Transport

  摘要：

  Artificial ligands of streptavidin (ALiS) with association constants of similar to 10(6) M-1 were discovered by high-throughput screening of our chemical library, and their binding characteristics, including X-ray crystal structure of the streptavidin complex, were determined. Unlike biotin and its derivatives, ALiS exhibits fast dissociation kinetics and excellent cell permeability. The streptavidin-ALiS system provides a novel, practical compound-dependent methodology for repeated reversible cycling of protein localization between intracellular organella.

  DOI：

  10.1021/jacs.5b05672
• 作为产物：
  描述：

  1',2'-dimethyl dethiobiotin 反应 5.0h， 生成 1',3'-dimethyl biotin
  参考文献：
  名称：

  Azoulay, Michel; Frappier, Francois; Marquet, Andree, Agricultural and Biological Chemistry, 1985, vol. 49, # 9, p. 2783 - 2786

  摘要：

  DOI：

文献信息

• 958. A search for biotin antagonists and the isolation of γ-biotin
  作者：A. B. A. Jansen、P. J. Stokes

  DOI：10.1039/jr9620004909

  日期：——
• Artificial Ligands of Streptavidin (ALiS): Discovery, Characterization, and Application for Reversible Control of Intracellular Protein Transport
  作者：Takuya Terai、Moe Kohno、Gaelle Boncompain、Shigeru Sugiyama、Nae Saito、Ryo Fujikake、Tasuku Ueno、Toru Komatsu、Kenjiro Hanaoka、Takayoshi Okabe、Yasuteru Urano、Franck Perez、Tetsuo Nagano

  DOI：10.1021/jacs.5b05672

  日期：2015.8.26

  Artificial ligands of streptavidin (ALiS) with association constants of similar to 10(6) M-1 were discovered by high-throughput screening of our chemical library, and their binding characteristics, including X-ray crystal structure of the streptavidin complex, were determined. Unlike biotin and its derivatives, ALiS exhibits fast dissociation kinetics and excellent cell permeability. The streptavidin-ALiS system provides a novel, practical compound-dependent methodology for repeated reversible cycling of protein localization between intracellular organella.
• Azoulay, Michel; Frappier, Francois; Marquet, Andree, Agricultural and Biological Chemistry, 1985, vol. 49, # 9, p. 2783 - 2786
  作者：Azoulay, Michel、Frappier, Francois、Marquet, Andree

  DOI：——

  日期：——