H-Trp-Phe-OMe | 198632-67-6

• 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: H-Trp-Phe-OMe
• 英文别名: (S)-2-[(S)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-3-phenyl-propionic acid methyl ester；methyl (2S)-2-[[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-3-phenylpropanoate
• CAS: 198632-67-6
• 化学式: C₂₁H₂₃N₃O₃
• 分子量: 365.432
• InChiKey: MLDMMCLBZPZHCX-HKUYNNGSSA-N

物化性质

• 沸点：
  632.9±55.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  H-Trp-Phe-OMe 在 ammonium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以0.06 g的产率得到环(L-苯丙氨酰-L-色氨酰)
  参考文献：
  名称：

  产黄青霉ΔroqA菌株的诱变方法可产生新的洛克福汀D类似物

  摘要：

  突变体：DHTD和roquefortine D类似物是通过与产黄青霉（P. chrysogenum）突变体进行突变而产生的，在该突变体中，HTD生物合成基因被删除。本研究的合成前体的选择突出了突变菌株在脱氢和亲电子芳族取代步骤中的特异性。

  DOI：

  10.1002/cbic.201402686
• 作为产物：
  描述：

  N-苄氧羰基-L-色氨酸 在 N-甲基吗啉 、 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 H-Trp-Phe-OMe
  参考文献：
  名称：

  缓冲条件下含色氨酸肽的串联电化学氧化叠氮/杂环化

  摘要：

  锰催化后期衍生化用于通过自由基叠氮化/杂环化级联构建叠氮取代的四唑并[1,5- a ]吲哚肽。这种电化学氧化策略可以在缓冲溶液中温和、高效、环保的条件下进行。

  DOI：

  10.1002/anie.202206308

文献信息

• Diketo acids and their amino acid/dipeptidic analogues as promising scaffolds for the development of bacterial methionine aminopeptidase inhibitors
  作者：Mir Mohammad Masood、Vijay K. Pillalamarri、Mohammad Irfan、Babita Aneja、Mohamad Aman Jairajpuri、Md. Zafaryab、M. Moshahid A. Rizvi、Umesh Yadava、Anthony Addlagatta、Mohammad Abid

  DOI：10.1039/c5ra03354c

  日期：——

  Diketo acids and their peptidic analogues were designed and synthesised as bacterial MetAP inhibitors. In the enzymatic assay, the representative compound 5e showed excellent inhibition of bacterial MetAPs with no cytotoxicity.

  二酮酸及其肽类类似物被设计并合成为细菌MetAP抑制剂。在酶活性测定中，代表性化合物5e显示出对细菌MetAPs的优秀抑制作用，且无细胞毒性。
• MITHRAMYCIN DERIVATIVES HAVING INCREASED SELECTIVITY AND ANTI-CANCER ACTIVITY
  申请人：University of Kentucky Research Foundation

  公开号：US20190083519A1

  公开（公告）日：2019-03-21

  Mithramycin side chain carboxylic acid (MTM-SA) derivative are provided, which include a substituted amino acid derivative, a substituted amino acid dipeptide derivative, or an unsubstituted dipeptide derivative. The MTM-SA derivatives are useful for treatment of cancer or neuro-diseases associated with an aberrant erythroblast transformation-specific transcription factor. Unique MTM-SA derivatives have increased selectively toward ETS transcription factor.

  米司麦霉素侧链羧酸（MTM-SA）衍生物包括一种取代氨基酸衍生物、一种取代氨基酸二肽衍生物或一种未取代的二肽衍生物。这些MTM-SA衍生物对于治疗与异常红细胞转化特异性转录因子相关的癌症或神经疾病很有用。独特的MTM-SA衍生物对ETS转录因子具有增强的选择性。
• Mithramycin derivatives having increased selectivity and anti-cancer activity
  申请人：University of Kentucky Research Foundation

  公开号：US11224609B2

  公开（公告）日：2022-01-18

  Mithramycin side chain carboxylic acid (MTM-SA) derivative are provided, which include a substituted amino acid derivative, a substituted amino acid dipeptide derivative, or an unsubstituted dipeptide derivative. The MTM-SA derivatives are useful for treatment of cancer or neuro-diseases associated with an aberrant erythroblast transformation-specific transcription factor. Unique MTM-SA derivatives have increased selectively toward ETS transcription factor.

  提供了米曲霉素侧链羧酸（MTM-SA）衍生物，其中包括取代的氨基酸衍生物、取代的氨基酸二肽衍生物或未取代的二肽衍生物。MTM-SA 衍生物可用于治疗与红细胞转化特异性转录因子异常有关的癌症或神经疾病。独特的 MTM-SA 衍生物对 ETS 转录因子的选择性增加。
• Development of Mithramycin Analogues with Increased Selectivity toward ETS Transcription Factor Expressing Cancers
  作者：Prithiba Mitra、Joseph M. Eckenrode、Abhisek Mandal、Amit K. Jha、Shaimaa M. Salem、Markos Leggas、Jürgen Rohr

  DOI：10.1021/acs.jmedchem.8b01107

  日期：2018.9.13

  Mithramycin A (1) was identified as the top potential inhibitor of the aberrant ETS transcription factor EWSFLI1, which causes Ewing sarcoma. Unfortunately, 1 has a narrow therapeutic window, compelling us to seek less toxic and more selective analogues. Here, we used MTMSA (2) to generate analogues via peptide coupling and fragment-based drug development strategies. Cytotoxicity assays in ETS and non-ETS dependent cell lines identified two dipeptide analogues, 60 and 61, with 19.1- and 15.6-fold selectivity, respectively, compared to 1.5-fold for 1. Importantly, the cytotoxicity of 60 and 61 is <100 nM in ETS cells. Molecular assays demonstrated the inhibitory capacity of these analogues against EWS-FLI1 mediated transcription in Ewing sarcoma. Structural analysis shows that positioning the tryptophan residue in a distal position improves selectivity, presumably via interaction with the ETS transcription factor. Thus, these analogues may present new ways to target transcription factors for clinical use.
• Novel antibiotics: C-2 symmetrical macrocycles inhibiting Holliday junction DNA binding by E. coli RuvC
  作者：Po-Shen Pan、Fiona A. Curtis、Chris L. Carroll、Irene Medina、Lisa A. Liotta、Gary J. Sharples、Shelli R. McAlpine

  DOI：10.1016/j.bmc.2006.03.028

  日期：2006.7.15

  Holliday junctions (HJs) are formed as transient DNA intermediates during site-specific and homologous recombination. Both of these genetic exchange pathways are critical for normal DNA metabolism and repair. Trapping HJs leads to bacterial cell death by preventing proper segregation of the resulting interlinked chromosomes. Macrocyclic peptides designed to target this intermediate were synthesized with the goal of identifying compounds with specificity for this unique molecular target. We discovered ten macrocycles, both hexameric and octameric peptides, capable of trapping HJs in vitro. Those macrocycles containing tyrosine residues proved most effective. These data demonstrate that C-2 symmetrical macrocycles offer excellent synthetic targets for the development of novel antibiotic agents. Furthermore, the active compounds identified provide valuable tools for probing different pathways of recombinational exchange. (c) 2006 Elsevier Ltd. All rights reserved.