N-acetyl-7'-bromo-D-tryptophan | 496929-98-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyl-7'-bromo-D-tryptophan
• 英文别名: Ac-7'-Br-D-Trp-OH；(2R)-2-acetamido-3-(7-bromo-1H-indol-3-yl)propanoic acid
• CAS: 496929-98-7
• 化学式: C₁₃H₁₃BrN₂O₃
• 分子量: 325.162
• InChiKey: TZHTUVZZNLKONV-LLVKDONJSA-N

物化性质

• 沸点：
  627.7±55.0 °C(Predicted)
• 密度：
  1.615±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-acetyl-7'-bromo-D-tryptophan 在 氢溴酸 作用下， 反应 3.0h， 以86.6%的产率得到7-溴-D-色氨酸
  参考文献：
  名称：

  Convenient synthesis of 7′ and 6′-bromo-d-tryptophan and their derivatives by enzymatic optical resolution using d-aminoacylase

  摘要：

  Compounds 7' and 61-bromo-D-tryptophan (1 and 2) which are important derivatives for the synthesis of the chloropeptin and kistamycin A, respectively, were conveniently synthesized by optical resolution from N-acetyl-7' and 6-bromo-DL-tryptophan ((RS)-5 and (RS)-14) using D-aminoacylase. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00909-2
• 作为产物：
  描述：

  1-溴-2-硝基苯 在 L-aminoacylase 、 cobalt(II) chloride 作用下， 以 四氢呋喃 、 phosphate buffer 、 溶剂黄146 为溶剂， 反应 32.33h， 生成 N-acetyl-7'-bromo-D-tryptophan
  参考文献：
  名称：

  Convenient synthesis of 7′ and 6′-bromo-d-tryptophan and their derivatives by enzymatic optical resolution using d-aminoacylase

  摘要：

  Compounds 7' and 61-bromo-D-tryptophan (1 and 2) which are important derivatives for the synthesis of the chloropeptin and kistamycin A, respectively, were conveniently synthesized by optical resolution from N-acetyl-7' and 6-bromo-DL-tryptophan ((RS)-5 and (RS)-14) using D-aminoacylase. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00909-2

文献信息

• Total Synthesis Guided Structure Elucidation of (+)‐Psychotetramine
  作者：Klement Foo、Timothy Newhouse、Ikue Mori、Hiromitsu Takayama、Phil S. Baran

  DOI：10.1002/anie.201008048

  日期：2011.3.14

  Solving the puzzles: Total synthesis played a key role in the elucidation of the stereochemistry and verification of the constitution of the complex polymeric natural product psychotetramine. The route features three powerful assembly processes that enabled four rounds of total synthesis‐guided structure determination. The pursuit of this alkaloid also led to an improved procedure for indole–aniline

  解谜：全合成在立体化学的阐明和复杂的聚合天然产物精神四胺的构成验证中发挥了关键作用。该路线具有三个强大的组装过程，可进行四轮全合成引导结构确定。对这种生物碱的追求也导致了吲哚-苯胺偶联的改进程序和精神三胺的高效对映选择性合成。
• Synthesis of Tripeptides Containing <scp>d</scp>-Trp Substituted at the Indole Ring, Assessment of Opioid Receptor Binding and in Vivo Central Antinociception
  作者：Rossella De Marco、Andrea Bedini、Santi Spampinato、Luca Gentilucci

  DOI：10.1021/jm5002925

  日期：2014.8.14

  The noncationizable tripeptide Ac-D-Trp-Phe-GlyNH2 was recently proposed as a novel minimal recognition motif for μ-opioid receptor. The introduction of different substituents (methyl, halogens, nitro, etc.) at the indole of D-Trp significantly influenced receptor affinities and resulted in serum stability and in a measurable effect on central antinociception in mice after ip administration.