Methanethiosulfonic acid S-{2-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-tert-butoxycarbonylamino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-ethyl} ester | 906641-04-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: Methanethiosulfonic acid S-{2-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-tert-butoxycarbonylamino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-ethyl} ester
• CAS: 906641-04-1
• 化学式: C₃₂H₅₆N₂O₇S₂
• 分子量: 644.938
• InChiKey: PAKDXEWVOYIUEP-HQGWNTEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  142.03
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methanethiosulfonic acid S-{2-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-tert-butoxycarbonylamino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-ethyl} ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 Methanethiosulfonic acid S-{2-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-amino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-ethyl} ester
  参考文献：
  名称：

  Design of novel synthetic MTS conjugates of bile acids for site-directed sulfhydryl labeling of cysteine residues in bile acid binding and transporting proteins

  摘要：

  The purpose of this study was to design bile acid-containing methanethiosulfonate (MTS) agents with appropriate physical attributes to effectively modify the cysteine residues present in the human apical sodium-dependent bile acid transporter. Four physical properties including surface area, molecular volume, Clog P, and dipole moment were calculated for each semiempirically optimized structure of NITS compounds. The specificity of the synthesized bile acid-MTS conjugate toward native cysteines and putative bile acid interacting domains of hASBT was supported by the effect of 1 mM cholyl-MTS, cholylglycyl-MTS, and 3-amino-cholyl-MTS on uptake activity, that displayed a significant decrease in TCA affinity (K-T = 69.9 +/- 4.5, 69.01 +/- 6.2, and 63.24 +/- 0.26 mu M and J(max) = 35.8 +/- 0.3, 24.03 +/- 1.22, 46.49 +/- 5.01 pmol mg protein min(-1), respectively). These compounds prove to be effective tools in probing the structural and functional effects of cysteine residues in bile acid binding and transporting proteins. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.050
• 作为产物：
  描述：

  (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-tert-Butoxycarbonylamino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 在 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 Methanethiosulfonic acid S-{2-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-tert-butoxycarbonylamino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-ethyl} ester
  参考文献：
  名称：

  Design of novel synthetic MTS conjugates of bile acids for site-directed sulfhydryl labeling of cysteine residues in bile acid binding and transporting proteins

  摘要：

  The purpose of this study was to design bile acid-containing methanethiosulfonate (MTS) agents with appropriate physical attributes to effectively modify the cysteine residues present in the human apical sodium-dependent bile acid transporter. Four physical properties including surface area, molecular volume, Clog P, and dipole moment were calculated for each semiempirically optimized structure of NITS compounds. The specificity of the synthesized bile acid-MTS conjugate toward native cysteines and putative bile acid interacting domains of hASBT was supported by the effect of 1 mM cholyl-MTS, cholylglycyl-MTS, and 3-amino-cholyl-MTS on uptake activity, that displayed a significant decrease in TCA affinity (K-T = 69.9 +/- 4.5, 69.01 +/- 6.2, and 63.24 +/- 0.26 mu M and J(max) = 35.8 +/- 0.3, 24.03 +/- 1.22, 46.49 +/- 5.01 pmol mg protein min(-1), respectively). These compounds prove to be effective tools in probing the structural and functional effects of cysteine residues in bile acid binding and transporting proteins. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.050