(4E,2S,3R)-2-amino-1,3,17-trihydroxy-17-(3,5-dinitrobenzoyl)-4-heptadecene | 448211-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4E,2S,3R)-2-amino-1,3,17-trihydroxy-17-(3,5-dinitrobenzoyl)-4-heptadecene
• CAS: 448211-01-6
• 化学式: C₂₄H₃₇N₃O₈
• 分子量: 495.573
• InChiKey: KCMJJPQDAFWAFR-ASTIYFOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  35.0
• 可旋转键数：
  19.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  179.06
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (4E,2S,3R)-2-amino-1,3,17-trihydroxy-17-(3,5-dinitrobenzoyl)-4-heptadecene 、 10-pyren-1-yldecanoyl 10-pyren-1-yldecanoate 以 四氢呋喃 为溶剂， 反应 18.0h， 以58%的产率得到(15R,16S,E)-15,17-dihydroxy-16-(10-(pyren-1-yl)decanamido)heptadec-13-en-1-yl 3,5-dinitrobenzoate
  参考文献：
  名称：

  Synthesis of a novel fluorescent ceramide analogue and its use in the characterization of recombinant ceramidase from Pseudomonas aeruginosa PA01

  摘要：

  Ceramidase (CDase) hydrolyses the N-acyl linkage of the sphingolipid ceramide. We synthesized the non-fluorescent ceramide analogue (4E,2S,3R)-2-N-(10-pyrenedecanoyl)-1,3,17-trihydroxy-17-(3,5-dinitrobenzoyl)-4-heptadecene (10) that becomes fluorescent upon hydrolysis of its N-acyl bond. This novel substrate was used to Study several kinetic aspects of the recombinant CDase from the pathogenic bacterium Pseudomonas aeruginosa PA01. Maximum CDase activity was observed above 1.5 muM substrate, with an apparent K-m or 0.5 +/- 0.1 muM and a turnover of 5.5 min(-1). CDase activity depends on divalent cations without a strong specificity. CDase is inhibited by sphingosine and by several sphingosine analogues. The lack of inhibition by several mammalian CDase inhibitors Such as D-erythro-MAPP, L-erythro-MAPP or N-oleoylethanolamine points to a novel active site and/or substrate binding region. The CDase assay described here offers the opportunity to develop and screen for specific bacterial CDase inhibitors of pharmaceutical interest. (C) 2002 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00206-7
• 作为产物：
  描述：

  2-[(12-bromododecyl)oxy]tetrahydro-2H-pyran 在 吡啶 、 盐酸 、 正丁基锂 、 Amberlyst 15 、 对甲苯磺酸 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 为溶剂， -78.0~20.0 ℃ 、2.67 kPa 条件下， 反应 150.0h， 生成 (4E,2S,3R)-2-amino-1,3,17-trihydroxy-17-(3,5-dinitrobenzoyl)-4-heptadecene
  参考文献：
  名称：

  Synthesis of a novel fluorescent ceramide analogue and its use in the characterization of recombinant ceramidase from Pseudomonas aeruginosa PA01

  摘要：

  Ceramidase (CDase) hydrolyses the N-acyl linkage of the sphingolipid ceramide. We synthesized the non-fluorescent ceramide analogue (4E,2S,3R)-2-N-(10-pyrenedecanoyl)-1,3,17-trihydroxy-17-(3,5-dinitrobenzoyl)-4-heptadecene (10) that becomes fluorescent upon hydrolysis of its N-acyl bond. This novel substrate was used to Study several kinetic aspects of the recombinant CDase from the pathogenic bacterium Pseudomonas aeruginosa PA01. Maximum CDase activity was observed above 1.5 muM substrate, with an apparent K-m or 0.5 +/- 0.1 muM and a turnover of 5.5 min(-1). CDase activity depends on divalent cations without a strong specificity. CDase is inhibited by sphingosine and by several sphingosine analogues. The lack of inhibition by several mammalian CDase inhibitors Such as D-erythro-MAPP, L-erythro-MAPP or N-oleoylethanolamine points to a novel active site and/or substrate binding region. The CDase assay described here offers the opportunity to develop and screen for specific bacterial CDase inhibitors of pharmaceutical interest. (C) 2002 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00206-7