(2R,3S)-2-(stearoylamino)-1,3-hexadecanediol | 214150-00-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2R,3S)-2-(stearoylamino)-1,3-hexadecanediol
• 英文别名: N-[(2R,3S)-1,3-dihydroxyhexadecan-2-yl]octadecanamide
• CAS: 214150-00-2
• 化学式: C₃₄H₆₉NO₃
• 分子量: 539.927
• InChiKey: LNDIPJDWEYOMHO-SAIUNTKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  38
• 可旋转键数：
  31
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-(stearoylamino)-1,3-hexadecanediol 在 盐酸 作用下， 生成 (2R,3S)-2-aminohexadecane-1,3-diol
  参考文献：
  名称：

  Lipase-Catalyzed Enantiomeric Resolution of Ceramides

  摘要：

  Lipase-catalyzed enantiomeric kinetic resolution of ceramides related to C-16-sphinganine and C-18-sphingenine is described. Two hydroxy groups in readily available racemic N-stearoyl-erythro-C-16-sphinganine were acetylated, and several kinds of lipases were screened for the hydrolysis of this substrate. Among them, a Burkholderia cepacia lipase (SC lipase A, Sumitomo Chemical Co., Ltd.) showed the highest reactivity and enantioselectivity. The rate of hydrolysis and selectivity were greatly affected by some additives. Especially, the combined use of a detergent, Triton X-100, and the solid support, Florisil, for immobilization showed the highest enantioselectivity (E = ca. 170), although the reaction rate turned low. Introduction of a double bond into the substrate (N-stearoyl-erythro-C-18-sphingenine) also retarded the hydrolysis. By utilizing the preferential hydrolysis of the acetate on the primary hydroxy group, another advantageous feature of this enzyme-catalyzed reaction, the resulting product could directly be used as the glycosyl acceptor for cerebroside synthesis.

  DOI：

  10.1021/jo980727u
• 作为产物：
  描述：

  肉豆蔻醛 在 palladium on activated charcoal 氢氧化钾 、 sodium acetate 、 ammonium formate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 (2R,3S)-2-(stearoylamino)-1,3-hexadecanediol
  参考文献：
  名称：

  Lipase-Catalyzed Enantiomeric Resolution of Ceramides

  摘要：

  Lipase-catalyzed enantiomeric kinetic resolution of ceramides related to C-16-sphinganine and C-18-sphingenine is described. Two hydroxy groups in readily available racemic N-stearoyl-erythro-C-16-sphinganine were acetylated, and several kinds of lipases were screened for the hydrolysis of this substrate. Among them, a Burkholderia cepacia lipase (SC lipase A, Sumitomo Chemical Co., Ltd.) showed the highest reactivity and enantioselectivity. The rate of hydrolysis and selectivity were greatly affected by some additives. Especially, the combined use of a detergent, Triton X-100, and the solid support, Florisil, for immobilization showed the highest enantioselectivity (E = ca. 170), although the reaction rate turned low. Introduction of a double bond into the substrate (N-stearoyl-erythro-C-18-sphingenine) also retarded the hydrolysis. By utilizing the preferential hydrolysis of the acetate on the primary hydroxy group, another advantageous feature of this enzyme-catalyzed reaction, the resulting product could directly be used as the glycosyl acceptor for cerebroside synthesis.

  DOI：

  10.1021/jo980727u

文献信息

• Production of optically active sphingoid compound
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP0869185A2

  公开（公告）日：1998-10-07

  An industrially advantageous production method of an optically active alcohol useful for cosmetics and medical supplies or production intermediates thereof using an esterase having an ability to selectively hydrolyze an optically active sphingoid compound.

  一种利用具有选择性水解光学活性鞘氨醇化合物能力的酯酶生产用于化妆品和医疗用品的光学活性醇或其生产中间体的具有工业优势的生产方法。
• US6184008B1
  申请人：——

  公开号：US6184008B1

  公开（公告）日：2001-02-06
• Lipase-Catalyzed Enantiomeric Resolution of Ceramides
  作者：Mikio Bakke、Masahiro Takizawa、Takeshi Sugai、Hiromichi Ohta

  DOI：10.1021/jo980727u

  日期：1998.10.1

  Lipase-catalyzed enantiomeric kinetic resolution of ceramides related to C-16-sphinganine and C-18-sphingenine is described. Two hydroxy groups in readily available racemic N-stearoyl-erythro-C-16-sphinganine were acetylated, and several kinds of lipases were screened for the hydrolysis of this substrate. Among them, a Burkholderia cepacia lipase (SC lipase A, Sumitomo Chemical Co., Ltd.) showed the highest reactivity and enantioselectivity. The rate of hydrolysis and selectivity were greatly affected by some additives. Especially, the combined use of a detergent, Triton X-100, and the solid support, Florisil, for immobilization showed the highest enantioselectivity (E = ca. 170), although the reaction rate turned low. Introduction of a double bond into the substrate (N-stearoyl-erythro-C-18-sphingenine) also retarded the hydrolysis. By utilizing the preferential hydrolysis of the acetate on the primary hydroxy group, another advantageous feature of this enzyme-catalyzed reaction, the resulting product could directly be used as the glycosyl acceptor for cerebroside synthesis.