Boc-His-Arg-OMe | 1184963-21-0

• 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-Arg-OMe
• 英文别名: methyl (2S)-5-(diaminomethylideneamino)-2-[[(2S)-3-(1H-imidazol-5-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]pentanoate
• CAS: 1184963-21-0
• 化学式: C₁₈H₃₁N₇O₅
• 分子量: 425.488
• InChiKey: YOJXHVFYJOGZLE-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  187
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-His-Arg-OMe 在 盐酸 、 水 作用下， 反应 0.25h， 以96%的产率得到L-His-L-Arg-OMe
  参考文献：
  名称：

  Synthesis and antimicrobial activities of His(2-aryl)-Arg and Trp-His(2-aryl) classes of dipeptidomimetics

  摘要：

  在这份通讯中，我们报告了超短肽类模拟物的设计、合成和体外抗菌活性。

  DOI：

  10.1039/c4md00041b
• 作为产物：
  描述：

  L-精氨酸 在 盐酸 、 endo-N-Hydroxy-5-norbornene-2,3-dicarboximide 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 反应 2.0h， 生成 Boc-His-Arg-OMe
  参考文献：
  名称：

  Synthesis and antimicrobial activities of His(2-aryl)-Arg and Trp-His(2-aryl) classes of dipeptidomimetics

  摘要：

  在这份通讯中，我们报告了超短肽类模拟物的设计、合成和体外抗菌活性。

  DOI：

  10.1039/c4md00041b

文献信息

• Discovery of Trp-His and His-Arg Analogues as New Structural Classes of Short Antimicrobial Peptides
  作者：Rohit K. Sharma、Ravi P. Reddy、Werner Tegge、Rahul Jain

  DOI：10.1021/jm900622d

  日期：2009.12.10

  Naturally occurring antimicrobial peptides contain a large number of amino acid residues, which limits their clinical applicability. In search of short antimicrobial peptides, which represent a possible alternative for lead structures to fight antibiotic resistant microbial infections, a series of synthetic peptide analogues based oil Trp-His and His-Arg structural frameworks have been prepared and found to be active against several Gram-negative and Gram-positive bacterial strains as well as against a fungal strain with MIC values of the most potent Structures in the range of 5-20 mu g/mL ((IC50 in the range of 1-5 mu g/mL). The synthesized peptides showed no cytotoxic effect in an MTT assay up to the highest test concentration of 200 mu g/mL. A combination of small size, presence of unnatural amino acids, high antimicrobial activity, and absence of cytotoxicity reveals the synthesized Trp-His and His-Arg analogues as promising candidates for novel antimicrobial therapeutics.
• Discovery of Short Peptides Exhibiting High Potency against <i>Cryptococcus neoformans</i>
  作者：Amit Mahindra、Nitin Bagra、Nishima Wangoo、Shabana I. Khan、Melissa R. Jacob、Rahul Jain

  DOI：10.1021/ml500011v

  日期：2014.4.10

  Rapid increase in the emergence of resistance against existing antifungal drugs created a need to discover new structural classes of antifungal agents. In this study we describe the synthesis of a new structural class of short antifungal peptidomimetcis, their activity, and plausible mechanism of action. The results of the study show that peptides lie and Ware more potent than the control drug amphotericin B, with no cytotoxicity to human cancer cells and noncancerous mammalian kidney cells. The selectivity of peptides to fungus is depicted by transmission electron microscopy studies, and it revealed that lie possibly disrupts the model membrane of the fungal pathogen.
• 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.
• Synthesis and antimicrobial activities of His(2-aryl)-Arg and Trp-His(2-aryl) classes of dipeptidomimetics
  作者：Amit Mahindra、Krishna K. Sharma、Dinesh Rathore、Shabana. I. Khan、Melissa R. Jacob、Rahul Jain

  DOI：10.1039/c4md00041b

  日期：——

  In this communication, we report the design, synthesis andin vitroantimicrobial activity of ultra short peptidomimetics.

  在这份通讯中，我们报告了超短肽类模拟物的设计、合成和体外抗菌活性。