(S)-2-((S)-2-Amino-4-methyl-pentanoylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester; hydrochloride | 143413-36-9

• 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: (S)-2-((S)-2-Amino-4-methyl-pentanoylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester; hydrochloride
• 英文别名: Leu-trp-ome hcl；methyl (2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoate;hydrochloride
• CAS: 143413-36-9
• 化学式: C₁₈H₂₅N₃O₃*ClH
• 分子量: 367.876
• InChiKey: UWXXREJDKHROOB-DMLYUBSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  97.2
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-((S)-2-Amino-4-methyl-pentanoylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester; hydrochloride 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 silver(l) oxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.5h， 生成 (6S,9S,12S)-methyl 12-((1H-indol-3-yl)methyl)-6-((2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1-(pyridin-2-yl)-1H-indol-3-yl) methyl)-9-isobutyl-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate
  参考文献：
  名称：

  Rhodium(III)-Catalyzed C–H Alkenylation: Access to Maleimide-Decorated Tryptophan and Tryptophan-Containing Peptides

  摘要：

  Maleimide is widely applied in many fields, especially in antibody-drug conjugations and peptide drugs. Herein, we develop a strategy for the C-H alkenylation of tryptophan and tryptophan-containing peptides, providing a synthetic route of decorating maleimide on peptides. The method has a high tolerance of functional groups and protecting groups. Furthermore, this method was applied to prepare peptide conjugation with molecules such as drugs and fluorescence probes. Moreover, macrocyclic peptides were obtained via this reaction.

  DOI：

  10.1021/acs.orglett.0c00086
• 作为产物：
  描述：

  Boc-Leu-Trp-OMe 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 生成 (S)-2-((S)-2-Amino-4-methyl-pentanoylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester; hydrochloride
  参考文献：
  名称：

  肾上腺素E的全合成

  摘要：

  Reniochalistatin E（1）是从海洋海绵Reniochalina stalagmitis分离的五个相关环肽之一。这些化合物的发现源于针对富含脯氨酸的生物活性化合物的鉴定的筛选程序。Reniochalistatin E是家族中唯一拥有色氨酸氨基酸残基的成员。鉴于观察到的1的细胞毒性，人们致力于开发合成1的途径。的第一全合成1已经在15步路线在一个整体5.0％的收率完成。结果显示，与天然样品相比，肾上腺素甲壳素E的合成样品对HeLa和RPMI-8226细胞系具有相似的活性50个值分别为16.9 vs 17.3μM和4.5 vs 4.9μM。有趣的是，两个合成的完全去保护的八肽都被合成为具有神经毒性的，它们都具有细胞毒性。该途径提供了一种手段来探究1与进一步生物学研究的结构与活性之间的关系。

  DOI：

  10.1021/acs.jnatprod.7b00656

文献信息

• Total Synthesis of Reniochalistatin E
  作者：Anthony Fatino、Giovanna Baca、Chamitha Weeramange、Ryan J. Rafferty

  DOI：10.1021/acs.jnatprod.7b00656

  日期：2017.12.22

  first total synthesis of 1 has been accomplished in a 15-step route in an overall 5.0% yield. The synthetic sample of reniochalistatin E was shown to have similar activity toward HeLa and RPMI-8226 cell lines compared to the natural sample, with IC50 values of 16.9 vs 17.3 μM and 4.5 vs 4.9 μM, respectively. Interestingly, both of the fully deprotected octapeptides constructed toward the synthesis of

  Reniochalistatin E（1）是从海洋海绵Reniochalina stalagmitis分离的五个相关环肽之一。这些化合物的发现源于针对富含脯氨酸的生物活性化合物的鉴定的筛选程序。Reniochalistatin E是家族中唯一拥有色氨酸氨基酸残基的成员。鉴于观察到的1的细胞毒性，人们致力于开发合成1的途径。的第一全合成1已经在15步路线在一个整体5.0％的收率完成。结果显示，与天然样品相比，肾上腺素甲壳素E的合成样品对HeLa和RPMI-8226细胞系具有相似的活性50个值分别为16.9 vs 17.3μM和4.5 vs 4.9μM。有趣的是，两个合成的完全去保护的八肽都被合成为具有神经毒性的，它们都具有细胞毒性。该途径提供了一种手段来探究1与进一步生物学研究的结构与活性之间的关系。
• Compounds with a sequence of three radicals, the central one being .alpha.-
  申请人：Polifarma S.p.A.

  公开号：US05504071A1

  公开（公告）日：1996-04-02

  Compounds of general formula A--B--C in which: A is a monovalent radical of a laevorotatory ring molecule; B is a bivalent radical of a laevorotatory .alpha.-aminoacid; and C is a monovalent radical of a laevorotatory aromatic molecule. The compounds show an anti-hypertensive, analgesic, immuno-modulating and antiinflammatory activity, they are resistant to enzyme hydrolysis and they can be used for the preparation of drugs for oral administration.

  通式为A--B--C的化合物，其中：A是左旋环分子的一价基团；B是左旋α-氨基酸的二价基团；C是左旋芳香分子的一价基团。这些化合物表现出抗高血压、镇痛、免疫调节和抗炎活性，它们对酶水解具有抵抗性，可用于制备口服药物。
• Phosphorus-containing inhibitors of endothelin converting enzyme: effects of the electronic nature of phosphorus on inhibitor potency
  作者：Stephen R. Bertenshaw、Roland S. Rogers、Michael K. Stern、Bryan H. Norman、William M. Moore、Gina M. Jerome、Linda M. Branson、John F. McDonald、Ellen G. McMahon、Maria A. Palomo

  DOI：10.1021/jm00053a023

  日期：1993.1
• Syntheses of [12]aneN3–oligopeptide conjugates as effective DNA condensation agents
  作者：Zhi-Fen Li、Zhi-Fo Guo、Hao Yan、Zhong-Lin Lu、Da-Yong Wu

  DOI：10.1016/j.bmc.2012.03.022

  日期：2012.5

  With the aim to develop effective and low toxicity DNA condensation agents, a series of oligopeptide derived macrocyclic polyamine [12]aneN(3) conjugates 7a-h center dot 3HCl have been designed and synthesized through multi-step amidation reactions. Structure-property study through gel electrophoresis proved that the conjugates containing high hydrophobic ending amino acids exhibited effective condensation ability at concentration of 150-250 mu M, which was further confirmed by dynamic light scattering and atomic force microscopy experiments. EB displacement assay, ionic salt effect, and structure-property relationship in gel electrophoresis indicated that DNA condensation resulted from both the electrostatic interaction of [12]aneN(3) unit and hydrogen-bonding/hydrophobic multi-interaction of oligopeptide moiety in the conjugates with DNA. The reversible condensation process and their low cytotoxicity suggest that the new condensing agents are potential for the development of non-viral vectors. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of [12]aneN3–dipeptide conjugates as metal-free DNA nucleases
  作者：Zhi-Fen Li、Hua-Long Chen、Li-Jun Zhang、Zhong-Lin Lu

  DOI：10.1016/j.bmcl.2012.01.075

  日期：2012.3

  In this Letter, a series of macrocyclic polyamine [12]aneN(3)-dipeptide conjugates as a new type of metal-free nucleases were synthesized and fully characterized with H-1 NMR, C-13 NMR, IR, and HR-MS. Results indicate that these conjugates can bind to calf thymus DNA mainly through electrostatic interaction and can cleave the plasmid DNA at 200 mu M ( pH 7.2, 37 degrees C), with an acceleration of 10(6)-fold via hydrolytic pathway. (C) 2012 Elsevier Ltd. All rights reserved.