(2R,3R)-3-azido-2-hydroxy-tridecanoic acid | 269411-13-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R)-3-azido-2-hydroxy-tridecanoic acid
• 英文别名: (2R,3R)-3-azido-2-hydroxytridecanoic acid
• CAS: 269411-13-4
• 化学式: C₁₃H₂₅N₃O₃
• 分子量: 271.36
• InChiKey: SUZNNGAXPKWCTM-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  71.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-azido-2-hydroxy-tridecanoic acid 在 palladium on activated charcoal WSCD*HCl 、 氢气 、 1-羟基苯并三唑一水物 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 N6-benzyloxycarbonyl-N2-tert-butoxycarbonyl-lysyl-γ-methyl-leucyl-[(2R,3R)-3-decyl-2-hydroxy-β-alanyl]-glycine ethyl ester
  参考文献：
  名称：

  Synthesis and Antifungal Activity of Rhodopeptin Analogues. 2. Modification of the West Amino Acid Moiety

  摘要：

  [GRAPHICS]Structure-activity relationships of the west amino acid modified analogues of rhodopeptins, novel antifungal tetrapeptide isolated from Rhodococcus species Mer-N1033, have been investigated, Among the analogues synthesized, 2,2-difluoro and 2-hydroxy derivatives retained the antifungal activity with better physical properties, i.e., solubility or acute toxicity.

  DOI：

  10.1021/ol005630k
• 作为产物：
  描述：

  methyl (E)-tridec-2-enoate 在 titanium(IV) isopropylate 、 calcium sulfate 、 sodium hydroxide 、 AD-mix-α 、 sodium azide 、 甲基磺酰胺 、 氢溴酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 、 叔丁醇 为溶剂， 生成 (2R,3R)-3-azido-2-hydroxy-tridecanoic acid
  参考文献：
  名称：

  Synthesis and Antifungal Activity of Rhodopeptin Analogues. 2. Modification of the West Amino Acid Moiety

  摘要：

  [GRAPHICS]Structure-activity relationships of the west amino acid modified analogues of rhodopeptins, novel antifungal tetrapeptide isolated from Rhodococcus species Mer-N1033, have been investigated, Among the analogues synthesized, 2,2-difluoro and 2-hydroxy derivatives retained the antifungal activity with better physical properties, i.e., solubility or acute toxicity.

  DOI：

  10.1021/ol005630k

文献信息

• Synthesis and Antifungal Activity of Rhodopeptin Analogues. 2. Modification of the West Amino Acid Moiety
  作者：Kiyoshi Nakayama、Haruko C. Kawato、Hiroaki Inagaki、Ryohei Nakajima、Akihiro Kitamura、Kazuhiko Someya、Toshiharu Ohta

  DOI：10.1021/ol005630k

  日期：2000.4.1

  [GRAPHICS]Structure-activity relationships of the west amino acid modified analogues of rhodopeptins, novel antifungal tetrapeptide isolated from Rhodococcus species Mer-N1033, have been investigated, Among the analogues synthesized, 2,2-difluoro and 2-hydroxy derivatives retained the antifungal activity with better physical properties, i.e., solubility or acute toxicity.