(E)-2-methyl-4-(tetrahydropyran-2-yloxy)but-2-enylamine | 196799-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (E)-2-methyl-4-(tetrahydropyran-2-yloxy)but-2-enylamine
• CAS: 196799-89-0
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: JJJJXZRXTOMQHK-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-4-(tetrahydropyran-2-yloxy)but-2-enylamine 在 磷酸-三乙胺 2:1 、 4-甲基苯磺酸吡啶 、 三乙胺 、 三氯乙腈 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 1.5h， 生成 (E)-(2-methylbut-2-enyl)carbamic acid 9H-fluoren-9-ylmethyl ester 4-diphosphate bis ammonium salt
  参考文献：
  名称：

  Inhibition of IspH, a [4Fe–4S]²⁺ Enzyme Involved in the Biosynthesis of Isoprenoids via the Methylerythritol Phosphate Pathway

  摘要：

  The MEP pathway, which is absent in animals but present in most pathogenic bacteria, in the parasite responsible for malaria and in plant plastids, is a target for the development of antimicrobial drugs. IspH, an oxygen-sensitive [4Fe-4S] enzyme, catalyzes the last step of this pathway and converts (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate (HMBPP) into the two isoprenoid precursors: isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). A crucial step in the mechanism of this enzyme is the binding of the C4 hydroxyl of HMBPP to the unique fourth iron site in the [4Fe-4S](2+) moiety. Here, we report the synthesis and the kinetic investigations of two new extremely potent inhibitors of E. coli IspH where the OH group of HMBPP is replaced by an amino and a thiol group. (E)-4-Mercapto-3-methylbut-2-en-1-yl diphosphate is a reversible tight-binding inhibitor of IspH with K-i = 20 +/- 2, nM. A detailed kinetic analysis revealed that (E)-4-amino-3-methylbut-2-en-1-yl diphosphate is a reversible slow-binding inhibitor of IspH with K-i = 54 +/- 19 nM. The slow binding behavior of this inhibitor is best described by a one-step mechanism with the slow step consisting of the formation of the enzyme-inhibitor (EI) complex.

  DOI：

  10.1021/ja309557s
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 叔丁基过氧化氢 、 4-甲基苯磺酸吡啶 、 硒脲酸 、 一水合肼 、 三苯基膦 、 水杨酸 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (E)-2-methyl-4-(tetrahydropyran-2-yloxy)but-2-enylamine
  参考文献：
  名称：

  Synthesis and evaluation of benzophenone-based photoaffinity labeling analogs of prenyl pyrophosphates containing stable amide linkages

  摘要：

  The syntheses of two photoactive prenyl pyrophosphate analogs (1a and 1b) that incorporate stable amide-linked benzophenones are described. Compound 1a contains a single isoprene (C-5) unit between the pyrophosphate and benzophenone functionalities while 1b contains a geranyl (C-10) moiety. Compounds 1a and 1b are competitive inhibitors of yeast farnesyl protein transferase with respect to farnesyl pyrophosphate and have K-I values of 6000 nM and 700 nM. Upon irradiation, [P-32]-1b preferentially labels the beta-subunits of yeast farnesyl protein transferase and human geranylgeranyl protein transferase. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00373-9