1,2-bis-(t-butyl-dimethyl-silanyloxy)-3-t-butyldisulfanyl-propane | 1017573-13-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1,2-bis-(t-butyl-dimethyl-silanyloxy)-3-t-butyldisulfanyl-propane
• CAS: 1017573-13-5
• 化学式: C₁₉H₄₄O₂S₂Si₂
• 分子量: 424.86
• InChiKey: KUFVUDVOXDFMLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,2-bis-(t-butyl-dimethyl-silanyloxy)-3-t-butyldisulfanyl-propane 在 水 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以2.0 g的产率得到2-(t-butyl-dimethyl-silanyloxy)-3-t-butyldisulfanyl-propan-1-ol
  参考文献：
  名称：

  Cyclic Peptide Inhibitors of Staphylococcal Virulence Prepared by Fmoc-Based Thiolactone Peptide Synthesis

  摘要：

  Virulence factor production in Staphylococcus aureus is largely under the control of the accessory gene regulator (ago quorum sensing system. There are four agr groups, all of which exhibit bacterial interference: each agr type synthesizes a cyclic autoinducing peptide (AIP) with a distinct sequence that activates its cognate AgrC receptor and inhibits activation of others. To better understand inhibitory AIP-AgrC interactions, we aimed to identify the minimal molecular determinants required to inhibit both non-cognate and cognate receptors. This minimization of the AIP pharmacophore also may have therapeutic relevance as the use of native AIPs to block virulence of non-cognate agr strains can prevent the establishment of an infection in vivo. We synthesized and evaluated the inhibitory activities of 10 AIP derivatives based on a truncated AIP analogue that inhibits all four agr types. To carry out the rapid, parallel synthesis of these peptides, we employed a new linker for Fmoc-based thioester peptide synthesis. Our results identify key structural elements that are necessary for AgrC inhibition and reveal key differences between non-cognate and cognate inhibitory requirements.

  DOI：

  10.1021/ja711126e
• 作为产物：
  描述：

  (RS)-3-tert-butyldithio-1,2-propanediol 、 叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,2-bis-(t-butyl-dimethyl-silanyloxy)-3-t-butyldisulfanyl-propane
  参考文献：
  名称：

  Cyclic Peptide Inhibitors of Staphylococcal Virulence Prepared by Fmoc-Based Thiolactone Peptide Synthesis

  摘要：

  Virulence factor production in Staphylococcus aureus is largely under the control of the accessory gene regulator (ago quorum sensing system. There are four agr groups, all of which exhibit bacterial interference: each agr type synthesizes a cyclic autoinducing peptide (AIP) with a distinct sequence that activates its cognate AgrC receptor and inhibits activation of others. To better understand inhibitory AIP-AgrC interactions, we aimed to identify the minimal molecular determinants required to inhibit both non-cognate and cognate receptors. This minimization of the AIP pharmacophore also may have therapeutic relevance as the use of native AIPs to block virulence of non-cognate agr strains can prevent the establishment of an infection in vivo. We synthesized and evaluated the inhibitory activities of 10 AIP derivatives based on a truncated AIP analogue that inhibits all four agr types. To carry out the rapid, parallel synthesis of these peptides, we employed a new linker for Fmoc-based thioester peptide synthesis. Our results identify key structural elements that are necessary for AgrC inhibition and reveal key differences between non-cognate and cognate inhibitory requirements.

  DOI：

  10.1021/ja711126e