3-[N6-biotinyl-N2-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol | 473758-70-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 3-[N6-biotinyl-N2-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol
• 英文别名: 3-[N⁶-biotinyl-N²-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol
• CAS: 473758-70-2
• 化学式: C₄₁H₆₄N₄O₇S
• 分子量: 757.048
• InChiKey: NUMXCQWKQOTZRM-WCPGCEICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  53.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  155.09
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  溴乙酸 、 3-[N6-biotinyl-N2-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol 在 4-二甲氨基吡啶 、 4 A molecular sieve 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.28h， 以99%的产率得到(3R)-3-[N⁶-biotinyl-N²-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol bromoacetate
  参考文献：
  名称：

  Synthesis of biotinylated retinoids for cross-linking and isolation of retinol binding proteins

  摘要：

  The synthesis of (3R)-3-[Boc-Lys(biotinyl)-O]-11-cis-retinol bromoacetate and 3-[Boc-Lys(biotinyl)-0]-all trans-retinol chloroacetate is described. These biotinylated retinoids a-re instrumental in labeling the retinol binding proteins (RBPs) via a nucleophilic displacement of the haloacetate by a residue in the binding site of the protein. The covalently linked biotin will allow for a facile isolation and purification of the protein on a streptavidin column thus rendering the protein ready for a tryptic digest followed by mass spectrometric analysis. The 11-cis retinoid was synthesized via metal reduction of an alkyne intermediate generated from a Homer-Wadsworth-Emmons (HWE) reaction whereas the all-trans was synthesized via two consecutive HWE couplings. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00667-1
• 作为产物：
  描述：

  N-叔丁氧羰基-N'-生物素-L-赖氨酸 在 4-二甲氨基吡啶 、 4 A molecular sieve 、 四丁基氟化铵 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 3-[N6-biotinyl-N2-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol
  参考文献：
  名称：

  Synthesis of biotinylated retinoids for cross-linking and isolation of retinol binding proteins

  摘要：

  The synthesis of (3R)-3-[Boc-Lys(biotinyl)-O]-11-cis-retinol bromoacetate and 3-[Boc-Lys(biotinyl)-0]-all trans-retinol chloroacetate is described. These biotinylated retinoids a-re instrumental in labeling the retinol binding proteins (RBPs) via a nucleophilic displacement of the haloacetate by a residue in the binding site of the protein. The covalently linked biotin will allow for a facile isolation and purification of the protein on a streptavidin column thus rendering the protein ready for a tryptic digest followed by mass spectrometric analysis. The 11-cis retinoid was synthesized via metal reduction of an alkyne intermediate generated from a Homer-Wadsworth-Emmons (HWE) reaction whereas the all-trans was synthesized via two consecutive HWE couplings. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00667-1