1,3-bis(((5-(iodomethyl)-2,2-dimethyl-1,3-dioxan-5-yl)methyl)thio)propane | 1504558-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-bis(((5-(iodomethyl)-2,2-dimethyl-1,3-dioxan-5-yl)methyl)thio)propane
• CAS: 1504558-91-1
• 化学式: C₁₉H₃₄I₂O₄S₂
• 分子量: 644.418
• InChiKey: DOPQVYBJJGXHAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,3-bis(((5-(iodomethyl)-2,2-dimethyl-1,3-dioxan-5-yl)methyl)thio)propane 在 盐酸 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 48.0h， 生成 [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：

  1,3-二碘丙烷 、 7,7-dimethyl-6,8-dioxa-2-thiaspiro[3.5]nonane 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 264.0h， 以75%的产率得到1,3-bis(((5-(iodomethyl)-2,2-dimethyl-1,3-dioxan-5-yl)methyl)thio)propane
  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