Fmoc-Agb(Boc)2 | 206183-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Agb(Boc)2
• 英文别名: Fmoc-norArg(Boc)2-OH；(2S)-4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid
• CAS: 206183-06-4
• 化学式: C₃₀H₃₈N₄O₈
• 分子量: 582.654
• InChiKey: FNEGEHCONNLNCC-QHCPKHFHSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  9

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  FMOC-N-L-BETA-二苯基丙氨酸 、 Fmoc-Agb(Boc)2 、 alkaline earth salt of/the/ methylsulfuric acid 在 N,N-二异丙基乙胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  膜解阳离子大环肽对多重耐药细菌和真菌的广谱活性

  摘要：

  由于治疗选择有限，多重耐药（MDR）菌株的出现给微生物感染的治疗带来了严重问题。抗菌肽（AMP）作为对抗多重耐药细菌和真菌感染的有前景的抗生素替代候选物而受到广泛关注。在此，我们提出了一系列小的两亲性膜活性环肽，部分由各种非遗传编码的亲水性和疏水性氨基酸组成。值得注意的是，先导环肽对耐药革兰氏阳性菌（MIC = 1.5–6.2 µg/mL）和革兰氏阴性菌（MIC = 12.5–25 µg/mL）和真菌（MIC = 3.1）表现出广谱活性。 –12.5 微克/毫升）。此外，先导肽表现出与标准抗生素相当的显着抗生物膜作用。溶血 (HC = 230 µg/mL) 和细胞毒性（100 µg/mL 对四种不同哺乳动物细胞的细胞活力 > 70%）测定结果表明，对微生物的选择性致死作用优于对哺乳动物细胞的选择性致死作用。钙黄绿素染料渗漏实验证实了 和 的膜溶解作用，并通过扫描电子显微镜进一步证实。通过采用核磁共振

  DOI：

  10.1016/j.ejps.2024.106776
• 作为产物：
  描述：

  、 1,3-二-BOC-2-(三氟甲基磺酰)胍 在 N-甲基-N-(三甲基硅烷基)三氟乙酰胺 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到Fmoc-Agb(Boc)2
  参考文献：
  名称：

  Helix formation and capping energetics of arginine analogs with varying side chain length

  摘要：

  Arginine (Arg) has been used for recognizing negatively charged biological molecules, cell penetration, and oligosaccharide mass signal enhancement. The versatility of Arg has inspired the need to develop Arg analogs and to research the structural effects of incorporating Arg analogs. Accordingly, we investigated the effect of Arg side chain length on helix formation by studying 12 Ala-based peptides containing the Arg analogs (S)-2-amino-6-guanidino-hexanoic acid (Agh), (S)-2-amino-4-guanidinobutyric acid (Agb), and (S)-2-amino-3-guanidinopropionic acid (Agp). Solid phase guanidinylation with orthogonal protection strategies was necessary to synthesize Agb- and Agp-containing peptides using Fmoc-based chemistry. The fraction helix for the peptides was determined by circular dichroism spectroscopy, and used to derive the statistical mechanical parameters and energetics for N-capping, C-capping, and helix propagation (propensity). All four Arg analogs were unfavorable for N-capping. The C-cap parameter followed the trend Agp < Agb < Arg < Agh, showing more favorable C-cap energetics with increasing side chain length. In contrast, helix propensity followed the trend Agp < Agb < Arg > Agh, highlighting the uniqueness of the Arg side chain length in helix formation. Molecular mechanics calculations and a survey on protein structures were consistent with the experimental results. Furthermore, calculations and survey both showed that the g- conformation for the chi(1) dihedral was present for the first two residues at the N-terminus of helices, but not favored in the center or C-terminus of helices due to sterics. These results should serve as the foundation for developing Arg-related bioactive compounds and technologies.

  DOI：

  10.1007/s00726-011-1064-2

文献信息

• Helix formation and capping energetics of arginine analogs with varying side chain length
  作者：Richard P. Cheng、Yi-Jen Weng、Wei-Ren Wang、Marc J. Koyack、Yuta Suzuki、Cheng-Hsun Wu、Po-An Yang、Hao-Chun Hsu、Hsiou-Ting Kuo、Prashant Girinath、Chun-Jen Fang

  DOI：10.1007/s00726-011-1064-2

  日期：2012.7

  Arginine (Arg) has been used for recognizing negatively charged biological molecules, cell penetration, and oligosaccharide mass signal enhancement. The versatility of Arg has inspired the need to develop Arg analogs and to research the structural effects of incorporating Arg analogs. Accordingly, we investigated the effect of Arg side chain length on helix formation by studying 12 Ala-based peptides containing the Arg analogs (S)-2-amino-6-guanidino-hexanoic acid (Agh), (S)-2-amino-4-guanidinobutyric acid (Agb), and (S)-2-amino-3-guanidinopropionic acid (Agp). Solid phase guanidinylation with orthogonal protection strategies was necessary to synthesize Agb- and Agp-containing peptides using Fmoc-based chemistry. The fraction helix for the peptides was determined by circular dichroism spectroscopy, and used to derive the statistical mechanical parameters and energetics for N-capping, C-capping, and helix propagation (propensity). All four Arg analogs were unfavorable for N-capping. The C-cap parameter followed the trend Agp < Agb < Arg < Agh, showing more favorable C-cap energetics with increasing side chain length. In contrast, helix propensity followed the trend Agp < Agb < Arg > Agh, highlighting the uniqueness of the Arg side chain length in helix formation. Molecular mechanics calculations and a survey on protein structures were consistent with the experimental results. Furthermore, calculations and survey both showed that the g- conformation for the chi(1) dihedral was present for the first two residues at the N-terminus of helices, but not favored in the center or C-terminus of helices due to sterics. These results should serve as the foundation for developing Arg-related bioactive compounds and technologies.
• Broad-spectrum activity of membranolytic cationic macrocyclic peptides against multi-drug resistant bacteria and fungi
  作者：Sandeep Lohan、Anastasia G. Konshina、Rakesh K. Tiwari、Roman G. Efremov、Innokentiy Maslennikov、Keykavous Parang

  DOI：10.1016/j.ejps.2024.106776

  日期：2024.6

  Antimicrobial peptides (AMPs) are drawing considerable attention as promising antibiotic alternative candidates to combat MDR bacterial and fungal infections. Herein, we present a series of small amphiphilic membrane-active cyclic peptides composed, in part, of various nongenetically encoded hydrophilic and hydrophobic amino acids. Notably, lead cyclic peptides and showed broad-spectrum activity against drug-resistant

  由于治疗选择有限，多重耐药（MDR）菌株的出现给微生物感染的治疗带来了严重问题。抗菌肽（AMP）作为对抗多重耐药细菌和真菌感染的有前景的抗生素替代候选物而受到广泛关注。在此，我们提出了一系列小的两亲性膜活性环肽，部分由各种非遗传编码的亲水性和疏水性氨基酸组成。值得注意的是，先导环肽对耐药革兰氏阳性菌（MIC = 1.5–6.2 µg/mL）和革兰氏阴性菌（MIC = 12.5–25 µg/mL）和真菌（MIC = 3.1）表现出广谱活性。 –12.5 微克/毫升）。此外，先导肽表现出与标准抗生素相当的显着抗生物膜作用。溶血 (HC = 230 µg/mL) 和细胞毒性（100 µg/mL 对四种不同哺乳动物细胞的细胞活力 > 70%）测定结果表明，对微生物的选择性致死作用优于对哺乳动物细胞的选择性致死作用。钙黄绿素染料渗漏实验证实了 和 的膜溶解作用，并通过扫描电子显微镜进一步证实。通过采用核磁共振