tert-butyl (SR)-4-(2-(1H-indol-3-yl)ethylamino)-3-fluoro-4-oxobutylcarbamate | 1186533-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl (SR)-4-(2-(1H-indol-3-yl)ethylamino)-3-fluoro-4-oxobutylcarbamate
• CAS: 1186533-02-7
• 化学式: C₁₉H₂₆FN₃O₃
• 分子量: 363.432
• InChiKey: MGDNNHFINQVZDA-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  83.22
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  色胺 、 (2S)-boc-4-amino-2-fluorobutyric acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以66%的产率得到tert-butyl (SR)-4-(2-(1H-indol-3-yl)ethylamino)-3-fluoro-4-oxobutylcarbamate
  参考文献：
  名称：

  DNA sequence selectivity of hairpin polyamide turn units

  摘要：

  A class of hairpin polyamides linked by 3,4-diaminobutyric acid, resulting in a beta-amine residue at the turn unit, showed improved binding affinities relative to their alpha-amino-gamma-turn analogs for particular sequences. We incorporated beta-amino-gamma-turns in six-ring polyamides and determined whether there are any sequence preferences under the turn unit by quantitative footprinting titrations. Although there was an energetic penalty for G.C and C.G base pairs, we found little preference for T.A over A.T at the beta-amino- gamma-turn position. Fluorine and hydroxyl substituted alpha-amino-gamma-turns were synthesized for comparison. Their binding affinities and specificities in the context of six-ring polyamides demonstrated overall diminished affinity and no additional specificity at the turn position. We anticipate that this study will be a baseline for further investigation of the turn subunit as a recognition element for the DNA minor groove. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.072