(3R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxyhexan-1-one-1-13C | 1422163-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxyhexan-1-one-1-13C
• CAS: 1422163-41-4
• 化学式: C₂₂H₃₅NO₃S₂Si
• 分子量: 454.731
• InChiKey: AFBQYDQJIDVRJX-CAMCHBEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  、 (3R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxyhexan-1-one-1-13C 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以56%的产率得到
  参考文献：
  名称：

  Investigation of Fungal Iterative Polyketide Synthase Functions Using Partially Assembled Intermediates

  摘要：

  Iterative polyketide synthases (PKSs) are large, multifunctional enzymes that resemble eukaryotic fatty acid synthases but can make highly functionalized secondary metabolites using complex and unresolved programming rules. During biosynthesis of the kinase inhibitor hypothemycin by Hypomyces subiculosus, a highly reducing iterative PKS, Hpm8, cooperates with a nonreducing iterative PKS, Hpm3, to construct the advanced intermediate dehydrozearalenol (DHZ). The identity of putative intermediates in the formation of the highly reduced hexaketide portion of DHZ were confirmed by incorporation of C-13-labeled N-acetylcysteamine (SNAC) thioesters using the purified enzymes. The results show that Hpm8 can accept SNAC thioesters of intermediates that are ready for transfer from its acyl carrier protein domain to its ketosynthase domain and assemble them into DHZ in cooperation with Hpm3. Addition of certain structurally modified analogues of intermediates to Hpm8 and Hpm3 can produce DHZ derivatives.

  DOI：

  10.1021/ja4001823
• 作为产物：
  描述：

  (S)-4-benzyl-N-acetyl-1,3-thiazolidine-2-thione 、 (S)-3-(tert-butyldimethylsilyloxy)butanal 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 以31%的产率得到(3S,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxyhexan-1-one-1-13C
  参考文献：
  名称：

  Investigation of Fungal Iterative Polyketide Synthase Functions Using Partially Assembled Intermediates

  摘要：

  Iterative polyketide synthases (PKSs) are large, multifunctional enzymes that resemble eukaryotic fatty acid synthases but can make highly functionalized secondary metabolites using complex and unresolved programming rules. During biosynthesis of the kinase inhibitor hypothemycin by Hypomyces subiculosus, a highly reducing iterative PKS, Hpm8, cooperates with a nonreducing iterative PKS, Hpm3, to construct the advanced intermediate dehydrozearalenol (DHZ). The identity of putative intermediates in the formation of the highly reduced hexaketide portion of DHZ were confirmed by incorporation of C-13-labeled N-acetylcysteamine (SNAC) thioesters using the purified enzymes. The results show that Hpm8 can accept SNAC thioesters of intermediates that are ready for transfer from its acyl carrier protein domain to its ketosynthase domain and assemble them into DHZ in cooperation with Hpm3. Addition of certain structurally modified analogues of intermediates to Hpm8 and Hpm3 can produce DHZ derivatives.

  DOI：

  10.1021/ja4001823