N-((2S,3R,5R)-1,3,5-trihydroxy-15-methylhexadecan-2-yl)undec-10-ynamide | 1616618-51-9

• 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: N-((2S,3R,5R)-1,3,5-trihydroxy-15-methylhexadecan-2-yl)undec-10-ynamide
• CAS: 1616618-51-9
• 化学式: C₂₈H₅₃NO₄
• 分子量: 467.733
• InChiKey: QXAQURJEEBQJDX-KWXIBIRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33.0
• 可旋转键数：
  23.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  89.79
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-((2S,3R,5R)-1,3,5-trihydroxy-15-methylhexadecan-2-yl)undec-10-ynamide 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 N-((2S,3R,5R)-3,5-bis(tert-butyldimethylsilyloxy)-1-hydroxy-15-methylhexadecan-2-yl)undec-10-ynamide
  参考文献：
  名称：

  Synthesis of the Rosette-Inducing Factor RIF-1 and Analogs

  摘要：

  Studies on the origin of animal multicellularity have increasingly focused on one of the closest living relatives of animals, the choanoflagellate Salpingoeca rosetta. Single cells of S. rosetta can develop into multicellular rosette-shaped colonies through a process of incomplete cytokinesis. Unexpectedly, the initiation of rosette development requires bacterially produced small molecules. Previously, our laboratories reported the planar structure and femtomolar rosette-inducing activity of one rosette-inducing small molecule, dubbed rosette-inducing factor 1 (RIF-1), produced by the Gram-negative Bacteroidetes bacterium Algoriphagus machipongonensis. RIF-1 belongs to the small and poorly explored class of sulfonolipids. Here, we report a modular total synthesis of RIF-1 stereoisomers and structural analogs. Rosette-induction assays using synthetic RIF-1 stereoisomers and naturally occurring analogs defined the absolute stereochemistry of RIF-1 and revealed a remarkably restrictive set of structural requirements for inducing rosette development.

  DOI：

  10.1021/ja5046692
• 作为产物：
  描述：

  10-十一碳炔酸 、 (2S,3R,5R) 1,3,5-trihydroxy-15-methylhexadecan-2-amine hydrochloride 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 以72%的产率得到N-((2S,3R,5R)-1,3,5-trihydroxy-15-methylhexadecan-2-yl)undec-10-ynamide
  参考文献：
  名称：

  Synthesis of the Rosette-Inducing Factor RIF-1 and Analogs

  摘要：

  Studies on the origin of animal multicellularity have increasingly focused on one of the closest living relatives of animals, the choanoflagellate Salpingoeca rosetta. Single cells of S. rosetta can develop into multicellular rosette-shaped colonies through a process of incomplete cytokinesis. Unexpectedly, the initiation of rosette development requires bacterially produced small molecules. Previously, our laboratories reported the planar structure and femtomolar rosette-inducing activity of one rosette-inducing small molecule, dubbed rosette-inducing factor 1 (RIF-1), produced by the Gram-negative Bacteroidetes bacterium Algoriphagus machipongonensis. RIF-1 belongs to the small and poorly explored class of sulfonolipids. Here, we report a modular total synthesis of RIF-1 stereoisomers and structural analogs. Rosette-induction assays using synthetic RIF-1 stereoisomers and naturally occurring analogs defined the absolute stereochemistry of RIF-1 and revealed a remarkably restrictive set of structural requirements for inducing rosette development.

  DOI：

  10.1021/ja5046692