2-amino-2-deoxy-1-O-hexadecyl-3-O-trityl-sn-glycerol

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-amino-2-deoxy-1-O-hexadecyl-3-O-trityl-sn-glycerol
• 英文别名: (R)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-amine；(2R)-1-hexadecoxy-3-trityloxypropan-2-amine
• 化学式: C₃₈H₅₅NO₂
• 分子量: 557.86
• InChiKey: XLHBZLWZBSOYHD-DIPNUNPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  41
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-2-deoxy-1-O-hexadecyl-3-O-trityl-sn-glycerol 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 N-((R)-1-acetyl-3-(1-hexadecyloxy)propan-2-yl)formamide
  参考文献：
  名称：

  Structure and Synthesis of a Unique Isonitrile Lipid Isolated from the Marine Mollusk Actinocyclus papillatus

  摘要：

  The first chemical study of an Actinocyclidae nudibranch, Actinocyclus papillatus, resulted in the isolation of (-)-actisonitrile (1), a lipid based on a 1,3-propanediol ether skeleton. The structure was established by spectroscopic methods, whereas the absolute configuration of the chiral center was determined by comparing the optical properties of natural actisonitrile with those of (+)- and (-)-synthetic enantiomers, opportunely prepared. Both (-)- and (+)-actisonitrile were tested in preliminary in vitro cytotoxicity bioassays on tumor and nontumor mammalian cells.

  DOI：

  10.1021/ol200377w
• 作为产物：
  描述：

  1-十六烷醇 在 吡啶 、 sodium azide 、 potassium tert-butylate 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-amino-2-deoxy-1-O-hexadecyl-3-O-trityl-sn-glycerol
  参考文献：
  名称：

  Structure and Synthesis of a Unique Isonitrile Lipid Isolated from the Marine Mollusk Actinocyclus papillatus

  摘要：

  The first chemical study of an Actinocyclidae nudibranch, Actinocyclus papillatus, resulted in the isolation of (-)-actisonitrile (1), a lipid based on a 1,3-propanediol ether skeleton. The structure was established by spectroscopic methods, whereas the absolute configuration of the chiral center was determined by comparing the optical properties of natural actisonitrile with those of (+)- and (-)-synthetic enantiomers, opportunely prepared. Both (-)- and (+)-actisonitrile were tested in preliminary in vitro cytotoxicity bioassays on tumor and nontumor mammalian cells.

  DOI：

  10.1021/ol200377w

文献信息

• Fluorescent organophosphonates as inhibitors of microbial lipases
  作者：Olga V. Oskolkova、Robert Saf、Elfriede Zenzmaier、Albin Hermetter

  DOI：10.1016/s0009-3084(03)00085-9

  日期：2003.10

  respective compounds contain perylene or nitrobenzoxadiazole as reporter fluorophores covalently bound to the omega-ends of the respective 2-acylamino- and alkoxy- residues. Their inhibitory effects on the activities of three selected lipases showing different substrate preferences were determined, including the lipases from Rhizopus oryzae, Pseudomonas species, and Pseudomonas cepacia. R. oryzae lipase

  合成了短链和长链的1-O-烷基-2-酰基氨基脱氧甘油-和烷氧基-烷基膦酸对硝基苯酯作为抑制剂，用于脂解酶的分析和机理研究。各个化合物包含per或硝基苯并恶二唑作为报告荧光团，其共价键合至各个2-酰基氨基-和烷氧基-残基的ω-末端。确定了它们对三种显示出不同底物偏好的所选脂肪酶活性的抑制作用，这些酶包括米根霉，假单胞菌和洋葱假单胞菌的脂肪酶。米曲霉脂肪酶与单链抑制剂的反应比双链脱氧甘油脂的反应好得多。相反，P。与其他抑制剂相比，ceepacia脂肪酶被含two的双链膦酸酯（XXII）灭活的程度更大，而假单胞菌属脂肪酶与本研究中使用的所有抑制剂均有效地相互作用且没有任何偏好。总之，不同的脂肪酶不仅对三酰基甘油底物而且对与其结构相关的抑制剂都显示出非常特征性的反应模式。因此，新型膦酸酯可能不仅是用于分析和识别已知脂解酶的有用工具，而且还可以用于发现生物样品中未知的脂肪酶/酯酶。不同的脂肪酶不仅对
• Structure and Synthesis of a Unique Isonitrile Lipid Isolated from the Marine Mollusk <i>Actinocyclus papillatus</i>
  作者：Emiliano Manzo、Marianna Carbone、Ernesto Mollo、Carlo Irace、Antonio Di Pascale、Yan Li、Maria Letizia Ciavatta、Guido Cimino、Yue-Wei Guo、Margherita Gavagnin

  DOI：10.1021/ol200377w

  日期：2011.4.15

  The first chemical study of an Actinocyclidae nudibranch, Actinocyclus papillatus, resulted in the isolation of (-)-actisonitrile (1), a lipid based on a 1,3-propanediol ether skeleton. The structure was established by spectroscopic methods, whereas the absolute configuration of the chiral center was determined by comparing the optical properties of natural actisonitrile with those of (+)- and (-)-synthetic enantiomers, opportunely prepared. Both (-)- and (+)-actisonitrile were tested in preliminary in vitro cytotoxicity bioassays on tumor and nontumor mammalian cells.