Boc-L-phenylalanyl-L-isoleucine-OMe | 297740-86-4

• 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: Boc-L-phenylalanyl-L-isoleucine-OMe
• 英文别名: L-Ile(OMe)-L-Phe(N-^tBoc)；Boc-HN-Phe-Ile-OMe；Boc-Phe-Ile-OMe；Me3COC(=O)Phe-Ile-OMe；N-Boc-L-Phe-L-Ile-OMe；methyl (2S,3S)-3-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]pentanoate
• CAS: 297740-86-4
• 化学式: C₂₁H₃₂N₂O₅
• 分子量: 392.495
• InChiKey: PUYDHGUIAYPVSR-XIRDDKMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-L-phenylalanyl-L-isoleucine-OMe 在 盐酸 作用下， 以 水 为溶剂， 反应 0.25h， 生成 H-Phe-Ile-OMe
  参考文献：
  名称：

  Microwave-assisted solution phase peptide synthesis in neat water

  摘要：

  在微波辐射下，使用TBTU/HOBt/DIEA作为耦合组合，在纯水中开发了一种环境友好的溶液相多肽合成方法。该方法的关键特点包括替代常见的毒性有机溶剂如DMF和NMP，使用更少的反应物，与N-α-Boc保护和N-α-Fmoc保护的氨基酸以及所有常用侧链保护基团兼容，反应时间短，且在高效和高纯度下实现无消旋合成。

  DOI：

  10.1039/c3ra43040e
• 作为产物：
  描述：

  N-[(1,1-二甲基乙氧基)羰基]-L-异亮氨酸甲酯 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 Boc-L-phenylalanyl-L-isoleucine-OMe
  参考文献：
  名称：

  来自Palurus ramossisimus的环肽生物碱。

  摘要：

  通过离心分配色谱法和常规分离方法相结合，从七叶锦葵的根中分离出七个子碱A型环肽生物碱。在MS和精细的NMR光谱分析的基础上，对并构造了新的结构的paliurines AF（1-6）。通过比较合成的二肽的（13）C NMR数据，证实了其末端二肽的立体化学。

  DOI：

  10.1021/np000136a

文献信息

• Solvent-free peptide synthesis assisted by microwave irradiation: environmentally benign synthesis of bioactive peptides
  作者：Amit Mahindra、Neha Patel、Nitin Bagra、Rahul Jain

  DOI：10.1039/c3ra46643d

  日期：——

  An efficient and facile, solvent-free peptide synthesis assisted by microwave irradiation, using DIC/HONB as the coupling reagent combination is reported. Key features of this original protocol are solvent-free synthesis, very short reaction time and scalability without affecting yield and purity. The versatility of the method was successfully demonstrated by synthesizing several biologically active

  报道了使用DIC / HONB作为偶联剂组合物的微波辐照辅助的有效且容易的，无溶剂的肽合成。该原始协议的关键特征是无溶剂合成，非常短的反应时间和可扩展性，而不会影响收率和纯度。通过以高纯度，高收率且不消旋地合成几种生物活性肽，成功证明了该方法的多功能性。
• Marine Natural Occurring 2,5-Diketopiperazines: Isolation, Synthesis and Optical Properties
  作者：Ali Al-Mourabit、Rémi Laville、Thanh Binh Nguyen、Céline Moriou、Sylvain Petek、Cécile Debitus

  DOI：10.3987/com-14-s(k)87

  日期：——

  potential rule as important class of multifunctional biomolecules. Their putative roles as signaling molecules in the chemical ecology context is more and more considered. Thus, determination of absolute configuration of cyclic dipeptides is of significant importance. As a part of our on-going research on bioactive natural compounds from Pacific Axinellidae marine sponges, a scrutinized study of secondary

  七种 2,5-二酮哌嗪 (DKPs) 从斐济海海绵 Acanthella 海绵中分离出来。NMR 和圆二色性 (CD) 与合成 LL DKP 的比较使我们能够明确地确定天然 DKP 的 LL 绝对构型。这项工作启动了天然 DKP 光学特性数据库的建立，包括比旋光度和 CD。2,5-二酮哌嗪 (DKPs) 是环状次级代谢物，直接由初级肽代谢物产生。它们已在饮料、食品和微生物中检测到。作为最小的环肽，DKPs 提供了有趣的生物学特性，例如感官、抗肿瘤、抗真菌、抗菌、防污和抗病毒活性。2 包括生物碱在内的许多天然代谢物是通过氧化和重排反应从二酮哌嗪生物合成得到的。它们代表了一种有趣的药物化学工具，因为它们的杂环核心为进一步的化学和立体化学修饰提供了良好的模板。脯氨酸 (Pro) 和精氨酸 (Arg) 单位通常存在于具有生物活性的 DKP 中。尽管 DKP 的兴趣越来越大，但它们的立体化学信息并没
• Synthesis, Cytotoxic and Antimicrobial Screening of a Proline-Rich Cyclopolypeptide
  作者：Rajiv Dahiya、Akhilesh Kumar、Rajul Gupta

  DOI：10.1248/cpb.57.214

  日期：——

  Present study describes the first total synthesis of a cyclic heptapeptide, stylisin 1 (8) via coupling of tetrapeptide Boc-L-tyrosinyl-L-prolyl-L-leucyl-L-proline-OH and tripeptide L-phenylalanyl-L-isoleucyl-L-proline-OMe followed by cyclization of linear heptapeptide segment. Structure elucidation of synthesized cyclopeptide was done on basis of detailed spectral as well as elemental analysis. From the results of pharmacological screening, it was concluded that cyclopeptide 8 possessed moderate cytotoxicity against Dalton's lymphoma ascites (DLA) and Ehrlich's ascites carcinoma (EAC) cell lines with IC50 (inhibitory concentration, 50%) values of 10.6 and 14.6 μM. Furthermore, cyclopeptide 8 exhibited moderate to good antimicrobial activity against Gram −ve (negative) bacteria Klebsiella pneumoniae and Pseudomonas aeruginosa, dermatophytes and Candida albicans with minimum inhibitory concentration (MIC) of 6 μg/ml.

  本研究描述了首个环七肽stylisin 1（8）的全程合成，通过四肽Boc-L-酪氨酰-L-脯氨酰-L-亮氨酰-L-脯氨酸-OH与三肽L-苯丙氨酰-L-异亮氨酰-L-脯氨酸-OMe的耦合，随后进行线性七肽片段的环化。合成环肽的结构阐明基于详细的谱学及元素分析。从药理筛选结果得出，环肽8对Dalton淋巴瘤腹水（DLA）和Ehrlich腹水癌（EAC）细胞系表现出中等细胞毒性，IC50（抑制浓度，50%）值分别为10.6和14.6 μM。此外，环肽8对革兰氏阴性菌肺炎克雷伯菌和铜绿假单胞菌、皮肤真菌及白色念珠菌表现出中等至良好的抗微生物活性，最小抑制浓度（MIC）为6 μg/ml。
• Lead Optimization of 2-Phenylindolylglyoxylyldipeptide Murine Double Minute (MDM)2/Translocator Protein (TSPO) Dual Inhibitors for the Treatment of Gliomas
  作者：Simona Daniele、Valeria La Pietra、Elisabetta Barresi、Salvatore Di Maro、Eleonora Da Pozzo、Marco Robello、Concettina La Motta、Sandro Cosconati、Sabrina Taliani、Luciana Marinelli、Ettore Novellino、Claudia Martini、Federico Da Settimo

  DOI：10.1021/acs.jmedchem.5b01767

  日期：2016.5.26

  In glioblastoma multiforme (GBM), translocator protein (TSPO) and murine double minute (MDM)2/p53 complex represent two druggable targets. We recently reported the first dual binder 3 possessing a higher anticancer effect in GBM cells than the standards PK11195 1 or Nutlin-3 2 singularly applied. Herein, through a structure activity relationship study, we developed derivatives 4-10 with improved potencies toward both TSPO and MDM2. As a result, compound 9: (i) reactivated the p53 functionality; (ii) inhibited the viability of two human GBM cells; (iii) impaired the proliferation of glioma cancer stem cells (CSCs), more resistant to chemotherapeutics and responsible of GBM recurrence; (iv) sensitized GBM cells and CSCs to the activity of temozolomide; (v) directed its effects preferentially toward tumor cells with respect to healthy ones. Thus, 9 may represent a promising cytotoxic agent, which is worthy of being further developed for a therapeutic approach against GBM, where the downstream p53 signaling is intact and TSPO is overexpressed.
• Design, synthesis and biological evaluation of novel <i>L</i>-isoserine tripeptide derivatives as aminopeptidase N inhibitors
  作者：Huili Pan、Kanghui Yang、Jian Zhang、Yingying Xu、Yuqi Jiang、Yumei Yuan、Xiaopan Zhang、Wenfang Xu

  DOI：10.3109/14756366.2012.680062

  日期：2013.8.1

  Aminopeptidase N (APN/CD13) is one of the essential proteins for tumour invasion, angiogenesis and metastasis as it is over-expressed on the surface of different tumour cells. Based on our previous work that L-isoserine dipeptide derivatives were potent APN inhibitors, we designed and synthesized L-isoserine tripeptide derivatives as APN inhibitors. Among these compounds, one compound 16l (IC50 = 2.51 +/- 0.2 +/- mu M) showed similar inhibitory effect compared with control compound Bestatin (IC50 = 6.25 +/- 0.4 mu M) and it could be used as novel lead compound for the APN inhibitors development as anticancer agents in the future.