(R)-undecanoic-4-d acid | 1262048-50-9

• 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: (R)-undecanoic-4-d acid
• CAS: 1262048-50-9
• 化学式: C₁₁H₂₂O₂
• 分子量: 187.287
• InChiKey: ZDPHROOEEOARMN-DLDGQBHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-undecanoic-4-d acid 、 magnesium,1,2-dihydropyrrol-2-ide,bromide 在 三苯基膦 、 sodium tetrahydroborate 作用下， 以78%的产率得到[4'-2H](4'R)-2-undecylpyrrole
  参考文献：
  名称：

  Stereochemical Elucidation of Streptorubin B

  摘要：

  Streptorubin B is a structurally remarkable member of the prodiginine group of antibiotics produced by several actinobacteria, including the model organism Streptomyces coelicolor A3(2). Transannular strain within the pyrrolophane structure of this molecule causes restricted rotation that gives rise to the possibility of (diastereomeric) atropisomers. Neither the relative nor the absolute stereochemistry of streptorubin B is known. NOESY NMR experiments were used to define the relative stereochemistry of the major atropisomer of streptorubin B center dot HCl in solution as anti. We exploited this finding together with our knowledge of streptorubin B biosynthesis in S. coelicolor to determine the absolute stereochemistry of the anti atropisomer. 2-Undecylpyrrole stereoselectively labeled with deuterium at C-4' was synthesized and fed to a mutant of S. coelicolor, which was unable to produce streptorubin B because it was blocked in 2-undecylpyrrole biosynthesis, and in which the genes responsible for the last two steps of streptorubin B biosynthesis were overexpressed. H-1 and H-2 NMR analysis of the stereoselectively deuterium-labeled streptorubin B center dot HCl produced by this mutasynthesis strategy allowed us to assign the absolute stereochemistry of the major (anti) atropisomer as 7'S. HPLC analyses of streptorubin B isolated from S. coelicolor on a homochiral stationary phase and comparisons with streptorubin B derived from an enantioselective synthesis showed that the natural product consists of an approximately 88:7:5 mixture of the (7'S, anti), (7'S, syn), and (7'R, anti) stereoisomers.

  DOI：

  10.1021/ja109164t
• 作为产物：
  描述：

  (S)-(+)-5-氧代-2-四氢呋喃羧酸 在 吡啶 、 硼氘化钠 、 碘代三甲硅烷 、 dimethyl sulfide borane 、 sodium 、 copper(l) cyanide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 氯仿 、 水 、 二甲基亚砜 为溶剂， 反应 17.75h， 生成 (R)-undecanoic-4-d acid
  参考文献：
  名称：

  Stereochemical Elucidation of Streptorubin B

  摘要：

  Streptorubin B is a structurally remarkable member of the prodiginine group of antibiotics produced by several actinobacteria, including the model organism Streptomyces coelicolor A3(2). Transannular strain within the pyrrolophane structure of this molecule causes restricted rotation that gives rise to the possibility of (diastereomeric) atropisomers. Neither the relative nor the absolute stereochemistry of streptorubin B is known. NOESY NMR experiments were used to define the relative stereochemistry of the major atropisomer of streptorubin B center dot HCl in solution as anti. We exploited this finding together with our knowledge of streptorubin B biosynthesis in S. coelicolor to determine the absolute stereochemistry of the anti atropisomer. 2-Undecylpyrrole stereoselectively labeled with deuterium at C-4' was synthesized and fed to a mutant of S. coelicolor, which was unable to produce streptorubin B because it was blocked in 2-undecylpyrrole biosynthesis, and in which the genes responsible for the last two steps of streptorubin B biosynthesis were overexpressed. H-1 and H-2 NMR analysis of the stereoselectively deuterium-labeled streptorubin B center dot HCl produced by this mutasynthesis strategy allowed us to assign the absolute stereochemistry of the major (anti) atropisomer as 7'S. HPLC analyses of streptorubin B isolated from S. coelicolor on a homochiral stationary phase and comparisons with streptorubin B derived from an enantioselective synthesis showed that the natural product consists of an approximately 88:7:5 mixture of the (7'S, anti), (7'S, syn), and (7'R, anti) stereoisomers.

  DOI：

  10.1021/ja109164t