Boc-His-His-OMe | 252372-06-8

• 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-His-His-OMe
• 英文别名: methyl (2S)-3-(1H-imidazol-5-yl)-2-[[(2S)-3-(1H-imidazol-5-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoate
• CAS: 252372-06-8
• 化学式: C₁₈H₂₆N₆O₅
• 分子量: 406.442
• InChiKey: JMRNVAONNQZJJV-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-His-His-OMe 在 N-甲基吗啉 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 methyl (2S)-2-[[(2S)-2-[[5-(5,6-dimethyl-1H-benzimidazol-2-yl)-2-hydroxybenzoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-(1H-imidazol-5-yl)propanoate
  参考文献：
  名称：

  具有抗菌，细胞毒性和驱虫潜力的新型苯并咪唑并肽的合成研究。

  摘要：

  在氯化铜的存在下，通过5,6-二甲基-6硝基硝基苯并咪唑与重氮化的取代/未取代的氨基苯甲酸相互作用，合成了四个取代的苯并咪唑基-苯甲酸/水杨酸5-8。将化合物5-8与不同的氨基酸酯盐酸盐/二肽/三肽/四肽甲酯偶联，得到新的苯并咪唑并肽衍生物5a-f，6a-h，7a-g和8a-g。所有新合成的化合物的结构都是基于分析，IR，（1）H NMR，（13）C NMR和质谱数据确定的。通过使用氢氧化锂（LiOH）进一步水解选定的肽酯衍生物，得到相应的酸衍生物5b（a）-d（a​​），6e（a）-g（a），7c（a）-e（a）和8e （a）-g（a）。筛选所有肽衍生物的抗微生物，驱虫和细胞毒性活性。几乎所有新合成的苯并咪唑类肽对所有三种earth均表现出中等至良好的驱虫活性，对病原性真菌白色念珠菌和黑曲霉，革兰氏阴性细菌铜绿假单胞菌和大肠杆菌具有良好的抗菌活性。化合物8g和8g（a）对道尔顿氏淋巴瘤腹

  DOI：

  10.1016/j.ejmech.2006.11.015
• 作为产物：
  描述：

  N-Boc-L-组氨酸 、 L-组氨酸甲酯 在 endo-N-Hydroxy-5-norbornene-2,3-dicarboximide 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 生成 Boc-His-His-OMe
  参考文献：
  名称：

  Stabilized cationic dipeptide capped gold/silver nanohybrids: Towards enhanced antibacterial and antifungal efficacy

  摘要：

  The nanoparticles of silver/gold and cationic peptides have been recognized as potent antimicrobials for long, but their combined effect has so far not been explored. The present study reports the green synthesis of short cationic dipeptide stabilized AuNPs/AgNPs based nanohybrid materials. It thoroughly investigates the effect of conjugation of short cationic peptides on the antimicrobial properties of metallic nanoparticles. In the context of the antimicrobial evaluation of synthesized nanoconjugates, it was observed that peptide capped AgNPs exhibited higher antimicrobial activity as compared to peptide capped AuNPs as well as native peptides and unconjugated metallic nanoparticles. Specifically, L-His-L-Arg-OMe capped AgNPs exhibited MIC of 0.50, 0.37 and 0.25 mu M against E.coli, S. aureus and S. typhimurium respectively and MIC of 0.80 and 10.00 mu M against C. albicans and C. glabrata respectively. These results indicate that synthetic dipeptides render AgNPs as better antimicrobial agents in comparison to the native AgNPs and positively charged dipeptides. In addition, the time kill profile of cationic peptide (L-His-L-Arg-OMe) capped AgNPs was found to be even better than the known antibiotics. The cytotoxic behavior of all synthesized nanoconjugates of cationic peptides was studied and was found to be within acceptable limits. The present study opens a completely new class of antimicrobials for combating a wide range of bacterial and fungal pathogens. Another interesting and crucial finding was that dipeptide capped AgNPs displayed maximum antimicrobial activity with observed approximate 2-10 fold reduction in nano formulation dosage against tested microbes. (C) 2017 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.colsurfb.2017.07.009

文献信息

• Microwave-assisted solution phase peptide synthesis in neat water
  作者：Amit Mahindra、Karthik Nooney、Shrikant Uraon、Krishna K. Sharma、Rahul Jain

  DOI：10.1039/c3ra43040e

  日期：——

  An environmentally benign protocol for solution phase peptide synthesis has been developed in neat water using TBTU/HOBt/DIEA as a coupling combination under microwave irradiation. Key features of this procedure are the replacement of commonly used toxic organic solvents like DMF and NMP, the use of lower amounts of reactants, compatibility with both N-α-Boc- and N-α-Fmoc-protected amino acids and all commonly used side-chain protective groups, short reaction time, and racemization-free synthesis in high yield and purity.

  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。
• Stabilized cationic dipeptide capped gold/silver nanohybrids: Towards enhanced antibacterial and antifungal efficacy
  作者：Manish Bajaj、Satish K. Pandey、Tamanna Nain、Surinder K. Brar、Prabhjot Singh、Shivakanksha Singh、Nishima Wangoo、Rohit K. Sharma

  DOI：10.1016/j.colsurfb.2017.07.009

  日期：2017.10

  The nanoparticles of silver/gold and cationic peptides have been recognized as potent antimicrobials for long, but their combined effect has so far not been explored. The present study reports the green synthesis of short cationic dipeptide stabilized AuNPs/AgNPs based nanohybrid materials. It thoroughly investigates the effect of conjugation of short cationic peptides on the antimicrobial properties of metallic nanoparticles. In the context of the antimicrobial evaluation of synthesized nanoconjugates, it was observed that peptide capped AgNPs exhibited higher antimicrobial activity as compared to peptide capped AuNPs as well as native peptides and unconjugated metallic nanoparticles. Specifically, L-His-L-Arg-OMe capped AgNPs exhibited MIC of 0.50, 0.37 and 0.25 mu M against E.coli, S. aureus and S. typhimurium respectively and MIC of 0.80 and 10.00 mu M against C. albicans and C. glabrata respectively. These results indicate that synthetic dipeptides render AgNPs as better antimicrobial agents in comparison to the native AgNPs and positively charged dipeptides. In addition, the time kill profile of cationic peptide (L-His-L-Arg-OMe) capped AgNPs was found to be even better than the known antibiotics. The cytotoxic behavior of all synthesized nanoconjugates of cationic peptides was studied and was found to be within acceptable limits. The present study opens a completely new class of antimicrobials for combating a wide range of bacterial and fungal pathogens. Another interesting and crucial finding was that dipeptide capped AgNPs displayed maximum antimicrobial activity with observed approximate 2-10 fold reduction in nano formulation dosage against tested microbes. (C) 2017 Elsevier B.V. All rights reserved.
• Synthetic studies on novel benzimidazolopeptides with antimicrobial, cytotoxic and anthelmintic potential
  作者：Rajiv Dahiya、Devender Pathak

  DOI：10.1016/j.ejmech.2006.11.015

  日期：2007.6

  presence of cupric chloride. The coupling of compounds 5-8 with different amino acid ester hydrochlorides/dipeptide/tripeptide/tetrapeptide methyl esters afforded novel benzimidazolopeptide derivatives 5a-f, 6a-h, 7a-g and 8a-g. The structures of all newly synthesized compounds were established on the basis of analytical, IR, (1)H NMR, (13)C NMR and mass spectral data. Selected peptide ester derivatives were

  在氯化铜的存在下，通过5,6-二甲基-6硝基硝基苯并咪唑与重氮化的取代/未取代的氨基苯甲酸相互作用，合成了四个取代的苯并咪唑基-苯甲酸/水杨酸5-8。将化合物5-8与不同的氨基酸酯盐酸盐/二肽/三肽/四肽甲酯偶联，得到新的苯并咪唑并肽衍生物5a-f，6a-h，7a-g和8a-g。所有新合成的化合物的结构都是基于分析，IR，（1）H NMR，（13）C NMR和质谱数据确定的。通过使用氢氧化锂（LiOH）进一步水解选定的肽酯衍生物，得到相应的酸衍生物5b（a）-d（a​​），6e（a）-g（a），7c（a）-e（a）和8e （a）-g（a）。筛选所有肽衍生物的抗微生物，驱虫和细胞毒性活性。几乎所有新合成的苯并咪唑类肽对所有三种earth均表现出中等至良好的驱虫活性，对病原性真菌白色念珠菌和黑曲霉，革兰氏阴性细菌铜绿假单胞菌和大肠杆菌具有良好的抗菌活性。化合物8g和8g（a）对道尔顿氏淋巴瘤腹