Z-(D)-Trp-NH2 | 168110-39-2

• 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: Z-(D)-Trp-NH2
• 英文别名: Cbz-D-Trp-NH₂；Z-D-Trp-NH2；benzyl N-[(2R)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate
• CAS: 168110-39-2
• 化学式: C₁₉H₁₉N₃O₃
• 分子量: 337.378
• InChiKey: GGRKLCWXRBTPLH-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Z-(D)-Trp-NH2 在 10percent Pd/C N-甲基吗啉 、 盐酸 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  New Active Series of Growth Hormone Secretagogues

  摘要：

  New growth hormone secretagogue (GHS) analogues were synthesized and evaluated for growth hormone releasing activity. This series derived from EP-51389 is based on a gem-diamino structure. Compounds that exhibited higher in vivo GH-releasing potency than hexarelin in rat (subcutaneous administration) were then tested per os in beagle dogs and for their binding affinity to human pituitary GHS receptors and to hGHS-R 1a. Compound 7 (JMV 1843, H-Aib-(D)-Trp-(D)-gTrp-formyl) showed high potency in these tests and was selected for clinical studies.(1)

  DOI：

  10.1021/jm020985q
• 作为产物：
  描述：

  N-苄氧羰基-D-色氨酸 在 氯甲酸乙酯 、 三乙胺 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 生成 Z-(D)-Trp-NH2
  参考文献：
  名称：

  （-）-Strictosidine和相关的吲哚生物碱糖苷的总合成。

  摘要：

  据报道糖基化的单萜类吲哚生物碱的集体合成。开发了一种高度非对映选择性的Pictet-Spengler反应，以α-氰基色胺和secologanin四乙酸酯为底物，然后进行还原性脱氰反应，用于合成（-）-strictosidine，这是生物合成的重要中间体。建立了此两步化学方法，替代了生物合成采用的严格的芥子碱合酶。此外，在进行化学和计算研究之后，提出了在我们新发现的Pictet-Spengler反应中诱导非对映选择性的过渡态。仅用10个步骤就完成了（-）-strictosidine的首次对映选择性全合成，

  DOI：

  10.1002/anie.202005748

文献信息

• Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1 S ,2 R )-tranylcypromine
  作者：Tetsuya Ezawa、Yuya Kawashima、Takuya Noguchi、Seunghee Jung、Nobuyuki Imai

  DOI：10.1016/j.tetasy.2017.10.015

  日期：2017.12

  Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement. (C) 2017 Elsevier Ltd. All rights reserved.
• New Active Series of Growth Hormone Secretagogues
  作者：Vincent Guerlavais、Damien Boeglin、Delphine Mousseaux、Catherine Oiry、Annie Heitz、Romano Deghenghi、Vittorio Locatelli、Antonio Torsello、Corrado Ghé、Filomena Catapano、Giampiero Muccioli、Jean-Claude Galleyrand、Jean-Alain Fehrentz、Jean Martinez

  DOI：10.1021/jm020985q

  日期：2003.3.1

  New growth hormone secretagogue (GHS) analogues were synthesized and evaluated for growth hormone releasing activity. This series derived from EP-51389 is based on a gem-diamino structure. Compounds that exhibited higher in vivo GH-releasing potency than hexarelin in rat (subcutaneous administration) were then tested per os in beagle dogs and for their binding affinity to human pituitary GHS receptors and to hGHS-R 1a. Compound 7 (JMV 1843, H-Aib-(D)-Trp-(D)-gTrp-formyl) showed high potency in these tests and was selected for clinical studies.(1)
• Total Syntheses of (−)‐Strictosidine and Related Indole Alkaloid Glycosides
  作者：Jukiya Sakamoto、Yuhei Umeda、Kenta Rakumitsu、Michinori Sumimoto、Hayato Ishikawa

  DOI：10.1002/anie.202005748

  日期：2020.8.3

  A collective synthesis of glycosylated monoterpenoid indole alkaloids is reported. A highly diastereoselective Pictet–Spengler reaction with α‐cyanotryptamine and secologanin tetraacetate as substrates, followed by a reductive decyanation reaction, was developed for the synthesis of (−)‐strictosidine, which is an important intermediate in biosynthesis. This two‐step chemical method was established

  据报道糖基化的单萜类吲哚生物碱的集体合成。开发了一种高度非对映选择性的Pictet-Spengler反应，以α-氰基色胺和secologanin四乙酸酯为底物，然后进行还原性脱氰反应，用于合成（-）-strictosidine，这是生物合成的重要中间体。建立了此两步化学方法，替代了生物合成采用的严格的芥子碱合酶。此外，在进行化学和计算研究之后，提出了在我们新发现的Pictet-Spengler反应中诱导非对映选择性的过渡态。仅用10个步骤就完成了（-）-strictosidine的首次对映选择性全合成，