S-Oxo-S<(methylthio)methyl>-D-cysteinol | 77826-38-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: S-Oxo-S<(methylthio)methyl>-D-cysteinol
• 英文别名: S-oxo-S-[(methylthio)methyl]-D-cysteinol；S-Oxo-S[(methylthio)methyl]-D-cysteinol；(2S)-2-amino-3-[(R)-methylsulfanylmethylsulfinyl]propan-1-ol
• CAS: 77826-38-1
• 化学式: C₅H₁₃NO₂S₂
• 分子量: 183.296
• InChiKey: XXKRUXWFOXGFQQ-XUOSJQGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-Oxo-S<(methylthio)methyl>-D-cysteinol 、 3-(2,4-二氧代-6-甲基-5-嘧啶基)丙烯酸 在 氯甲酸乙酯 、 三乙胺 作用下， 生成 司帕索霉素
  参考文献：
  名称：

  Total synthesis of the antibiotic sparsomycin, a modified uracil amino acid monoxodithioacetal

  摘要：

  DOI：

  10.1021/jo00329a027
• 作为产物：
  描述：

  [(S)-1-Hydroxymethyl-2-((R)-methylsulfanylmethanesulfinyl)-ethyl]-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 反应 1.0h， 以85.9%的产率得到S-Oxo-S<(methylthio)methyl>-D-cysteinol
  参考文献：
  名称：

  Synthesis and biological activity of S-oxo-[(methylthio)-methyl]cysteinols

  摘要：

  A convenient route was developed to synthesize S-oxo-[(methylthio)-methyl]cysteitiols on a large scale from cheap L-serine as the starting material. The structures of diastereoisomers were determined by NMR, CD spectra, and X-ray diffraction analysis. All four diastereoisomers were examined for their ability to inhibit certain bacteria from growing. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.089

文献信息

• Synthesis of sparsomycin derivatives, addressing its binding to the large ribosomal subunit
  作者：L. A. G. M. van den Broek、A. J. J. Antonisse、H. C. J. Ottenheijm、A. San Felix、E. Lázaro、J. P. G. Ballesta、P. Lelieveld

  DOI：10.1002/recl.19921110401

  日期：——

  Apparently, the uracil ring plays an important role in the interaction of sparsomycin with the ribosomal peptidyl transferase and its unmodified presence is crucial for displaying activity. The photoprobes, carrying modifications in the “eastern C” fragment of 1, do interact with the ribosome, but less effectively than sparsomycin itself.

  化合物的合成14-19，6- methyluracilacryloyl衍生物，和27-29，抗肿瘤抗生素稀疏霉素光反应性叠氮芳基类似物（1）中描述。1的6-甲基尿嘧啶丙烯酰基部分的所有修饰都是通过选择性还原或通过选择性的6的N-和O-甲基化来实现的（方案2）。合成方案中与光亲和性类似物的关键步骤是使氯甲基亚砜20和21与在液氨中得到适当保护的胱胺22反应，得到由Sparsomycin N保护的胺分别如图23和24所示（方案4）。随后，光反应基团即。一个p -azidosalicylyl和4-叠氮基-2-硝基苯基，分别加上这些胺。为了评估所制备化合物的生物学活性，研究了两种无细胞测定法中蛋白质生物合成的抑制，液体培养基中大肠杆菌的细胞生长抑制和软琼脂中鼠白血病L1210菌落形成的抑制。在的“西方”片段引入的所有变型1使药物失去生物学活性。显然，尿嘧啶环在稀疏霉素与核糖体肽基转移酶的相互作用中
• Total synthesis of the antibiotic sparsomycin, a modified uracil amino acid monoxodithioacetal
  作者：Harry C. J. Ottenheijm、Rob M. J. Liskamp、Simon P. J. M. Van Nispen、Hans A. Boots、Marian W. Tijhuis

  DOI：10.1021/jo00329a027

  日期：1981.7
• Synthesis and biological activity of S-oxo-[(methylthio)-methyl]cysteinols
  作者：Zhen Xi、Xiao-Feng Cheng、Wen-Bin Chen、Li-Qiang Cao

  DOI：10.1016/j.tetlet.2006.03.089

  日期：2006.5

  A convenient route was developed to synthesize S-oxo-[(methylthio)-methyl]cysteitiols on a large scale from cheap L-serine as the starting material. The structures of diastereoisomers were determined by NMR, CD spectra, and X-ray diffraction analysis. All four diastereoisomers were examined for their ability to inhibit certain bacteria from growing. (c) 2006 Elsevier Ltd. All rights reserved.