3,3,17,17-tetramethyl-2,4,16,18-tetraoxa-8,12,21,25-tetrathiadispiro[5.7.514.76]hexacosane | 328289-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3,17,17-tetramethyl-2,4,16,18-tetraoxa-8,12,21,25-tetrathiadispiro[5.7.514.76]hexacosane
• CAS: 328289-25-4
• 化学式: C₂₂H₄₀O₄S₄
• 分子量: 496.821
• InChiKey: PUHHKINTWKEWSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3,17,17-tetramethyl-2,4,16,18-tetraoxa-8,12,21,25-tetrathiadispiro[5.7.514.76]hexacosane 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 以98%的产率得到[3,11,11-Tris(hydroxymethyl)-1,5,9,13-tetrathiacyclohexadec-3-yl]methanol
  参考文献：
  名称：

  Robust Affinity Standards for Cu(I) Biochemistry

  摘要：

  The measurement of reliable Cu(I) protein binding affinities requires competing reference ligands with similar binding strengths; however, the literature on such reference ligands is not only sparse but often conflicting. To address this deficiency, we have created and characterized a series of water-soluble monovalent copper ligands, MCL-1, MCL-2, and MCL-3, that form well-defined, air-stable, and colorless complexes with Cu(I) in aqueous solution. X-ray structural data, electrochemical measurements, and an extensive network of equilibrium titrations showed that all three ligands form discrete Cu(I) complexes with 1:1 stoichiometry and are capable of buffering Cu(I) concentrations between 10(-10) and 10(-7) M. As most Cu(I) protein affinities have been obtained from competition experiments with bathocuproine disulfonate or 2,2'-bicinchoninic acid, we further calibrated their Cu(I) stability constants against the MCL series. To demonstrate the application of these reagents, we determined the Cu(I) binding affinity of CusF (log K = 14.3 +/- 0.1), a periplasmic metalloprotein required for the detoxification of elevated copper levels in Escherichia coli. Altogether, this interconnected set of affinity standards establishes a reliable foundation that will facilitate the precise determination of Cu(I) binding affinities of proteins and small-molecule ligands.

  DOI：

  10.1021/ja408827d
• 作为产物：
  描述：

  1,3-丙二硫醇 、 1,3-bis(((5-(iodomethyl)-2,2-dimethyl-1,3-dioxan-5-yl)methyl)thio)propane 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以65%的产率得到3,3,17,17-tetramethyl-2,4,16,18-tetraoxa-8,12,21,25-tetrathiadispiro[5.7.514.76]hexacosane
  参考文献：
  名称：

  Robust Affinity Standards for Cu(I) Biochemistry

  摘要：

  The measurement of reliable Cu(I) protein binding affinities requires competing reference ligands with similar binding strengths; however, the literature on such reference ligands is not only sparse but often conflicting. To address this deficiency, we have created and characterized a series of water-soluble monovalent copper ligands, MCL-1, MCL-2, and MCL-3, that form well-defined, air-stable, and colorless complexes with Cu(I) in aqueous solution. X-ray structural data, electrochemical measurements, and an extensive network of equilibrium titrations showed that all three ligands form discrete Cu(I) complexes with 1:1 stoichiometry and are capable of buffering Cu(I) concentrations between 10(-10) and 10(-7) M. As most Cu(I) protein affinities have been obtained from competition experiments with bathocuproine disulfonate or 2,2'-bicinchoninic acid, we further calibrated their Cu(I) stability constants against the MCL series. To demonstrate the application of these reagents, we determined the Cu(I) binding affinity of CusF (log K = 14.3 +/- 0.1), a periplasmic metalloprotein required for the detoxification of elevated copper levels in Escherichia coli. Altogether, this interconnected set of affinity standards establishes a reliable foundation that will facilitate the precise determination of Cu(I) binding affinities of proteins and small-molecule ligands.

  DOI：

  10.1021/ja408827d