(S)-2,4-二[[芴甲氧羰基]氨基]丁酸 | 201473-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (S)-2,4-二[[芴甲氧羰基]氨基]丁酸
• 中文别名: (2S)-2,4-二[[(9H-芴-9-基甲氧基)羰基]氨基]-丁酸
• 英文名称: N^α,N^ε-bis(9-fluorenylmethoxycarbonyl)-L-diaminobutyric acid
• 英文别名: N-α-N-γ-bis-(9-fluorenylmethyloxycarbonyl)-L-2,4-diaminobutyric acid；Fmoc-L-Dab(Fmoc)-OH；Fmoc-Dab(Fmoc)-OH；(2S)-2,4-bis(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid
• CAS: 201473-83-8
• 化学式: C₃₄H₃₀N₂O₆
• 分子量: 562.622
• InChiKey: ALZDIZDLDRWFAC-HKBQPEDESA-N

物化性质

• 沸点：
  824.9±65.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

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

反应信息

• 作为反应物：
  描述：

  (S)-2,4-二[[芴甲氧羰基]氨基]丁酸 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-6-[bis[3-(5-nitro-1,3-dioxobenzo[de]isoquinolin-2-yl)propyl]amino]-2-[3-(5-nitro-1,3-dioxobenzo[de]isoquinolin-2-yl)propylamino]hexanoic acid
  参考文献：
  名称：

  固相有机合成法一步一步合成医药上重要的1,8-萘二甲酰亚胺肽

  摘要：

  描述了一种短合成新的医学上重要的单，双和三，1,8-萘二甲酰亚胺肽基衍生物的新方法。该方法有效地产生具有可变间隔区长度和在所需位置的带电，极性或疏水残基的1，8-萘二甲酰亚胺，其可以增加结合亲和力，构象稳定性，细胞内转运和/或生物活性。在这项工作中报道的合成途径既通用又适用，并且大大扩展了潜在的1,8-萘二甲酰亚胺抗癌候选药物的范围。

  DOI：

  10.1016/j.tetlet.2012.08.007

文献信息

• A two-step synthesis of medicinally-important 1,8-naphthalimide peptidyls by solid phase organic synthesis
  作者：Tamara Brider、Gary Gellerman

  DOI：10.1016/j.tetlet.2012.08.007

  日期：2012.10

  A new approach for a short synthesis of novel medicinally-important mono-, bis- and tris-1,8-naphthalimide peptidyl derivatives is described. The method generates efficiently 1,8-naphthalimides with variable spacer lengths and charged, polar or hydrophobic residues at desired positions, which can increase binding affinity, conformational stability, intracellular transport and/or biological activity

  描述了一种短合成新的医学上重要的单，双和三，1,8-萘二甲酰亚胺肽基衍生物的新方法。该方法有效地产生具有可变间隔区长度和在所需位置的带电，极性或疏水残基的1，8-萘二甲酰亚胺，其可以增加结合亲和力，构象稳定性，细胞内转运和/或生物活性。在这项工作中报道的合成途径既通用又适用，并且大大扩展了潜在的1,8-萘二甲酰亚胺抗癌候选药物的范围。
• [EN] LINEAR ASSEMBLIES BRANCHED ASSEMBLIES, MACROCYCLES AND COVALENT BUNDLES OF FUNCTIONALIZED BIS-PEPTIDES<br/>[FR] ENSEMBLES LINÉAIRES, ENSEMBLES RAMIFIÉS, MACROCYCLES ET FAISCEAUX COVALENTS DE BIS-PEPTIDES FONCTIONNALISÉS
  申请人：UNIV TEMPLE

  公开号：WO2012158200A1

  公开（公告）日：2012-11-22

  Provided is a macromolecule comprising two or more functionalized bis-peptides connected by one or more linkers, and methods of making thereof. In some embodiments, the functionalized bis-peptides are covalently attached to one or more functionalized bis-peptides to form linear strings of functionalized bis-peptides, macrocycles of functionalized bis-peptides, three-dimensional networks of functionalized bis-peptides, and combinations of any of these. Also provided is a macromolecule comprising two or more bis-peptides connected by one or more linkers, and methods of making thereof. In some embodiments, the bis-peptides comprise non-functionalized bis-peptides, functionalized bis-peptides or a combination of both functionalized and non-functionalized bis-peptides. In some embodiments, the bis-peptides are covalently attached to one or more bis-peptides to form linear strings of bis-peptides, macrocycles of bis-peptides, three-dimensional networks of bis-peptides, and combinations of any of these.

  提供的是一种大分子，包括由两个或更多个经功能化的双肽通过一个或多个连接物连接在一起，并制备方法。在某些实施例中，经功能化的双肽被共价地连接到一个或多个经功能化的双肽上，形成经功能化的双肽的线性链、经功能化的双肽的大环、经功能化的双肽的三维网络，以及这些的任意组合。还提供了一种大分子，包括由两个或更多个双肽通过一个或多个连接物连接在一起，并制备方法。在某些实施例中，双肽包括非功能化的双肽、经功能化的双肽或经功能化和非功能化双肽的组合。在某些实施例中，双肽被共价地连接到一个或多个双肽上，形成双肽的线性链、双肽的大环、双肽的三维网络，以及这些的任意组合。
• Melanocortin Receptor-Specific Peptides
  申请人：AstraZeneca AB

  公开号：US20150252077A1

  公开（公告）日：2015-09-10

  The invention relates to melanocortin receptor-specific cyclic peptides of Formula (I) or a pharmaceutically acceptable salt thereof, where R 1 , R 2 , R 3 , R 4a , R 4b , R 4c , R 5 , x and y are as defined in the specification. These compounds are particularly useful in the treatments of energy homeostasis and metabolism related (e.g. diabetes), food intake related and/or energy balance and body weight related diseases, disorders and/or conditions, including obesity, overweight and diseases, disorders and/or conditions associated with obesity and/or overweight, such as type 2 diabetes and metabolic syndrome.

  本发明涉及公式（I）的黑素皮质素受体特异性环肽或其药学上可接受的盐，其中R1、R2、R3、R4a、R4b、R4c、R5、x和y如规范中所定义。这些化合物在能量稳态和代谢相关（例如糖尿病）、食物摄入相关和/或能量平衡和体重相关的疾病、疾病和/或状况，包括肥胖、超重以及与肥胖和/或超重相关的疾病、疾病和/或状况的治疗中特别有用，例如2型糖尿病和代谢综合征。
• Spiroligomer‐Based Macrocycles for Atomically Precise Membranes
  作者：Yihui Xie、Danni Luo、Jesse A. Wiener、Alexander B. Koval、Conrad T. Pfeiffer、Christian E. Schafmeister

  DOI：10.1002/anie.202302809

  日期：2023.7.3

  Here, we report a new class of peptidomimetic macrocycles with well‐defined three‐dimensional structures and low conformational flexibility. They are assembled from fused‐ring spiro‐ladder oligomers (spiroligomers) by modular solid‐phase synthesis. Two‐dimensional nuclear magnetic resonance confirms their shape persistency. Triangular macrocycles of tunable sizes assemble into membranes with atomically precise pores, which exhibit size and shape‐dependent molecular sieving towards a series of structurally similar compounds. The exceptional structural diversity and stability of spiroligomer‐based macrocycles will be explored for more applications.

  摘要我们在此报告了一类新的拟肽大环，它们具有明确的三维结构和较低的构象灵活性。它们是通过模块化固相合成法由融合环螺梯形低聚物（螺梯形低聚物）组装而成的。二维核磁共振证实了它们的形状持久性。尺寸可调的三角形大环组装成具有原子精度孔隙的膜，对一系列结构相似的化合物表现出与尺寸和形状相关的分子筛分作用。我们将探索基于螺配体的大环的特殊结构多样性和稳定性，使其应用于更多领域。
• Development of dilipid polymyxins: Investigation on the effect of hydrophobicity through its fatty acyl component
  作者：Ronald Domalaon、Liam Berry、Quinn Tays、George G. Zhanel、Frank Schweizer

  DOI：10.1016/j.bioorg.2018.07.018

  日期：2018.10

  Continuous development of new antibacterial agents is necessary to counter the problem of antimicrobial resistance. Polymyxins are considered as drugs of last resort to combat multidrug-resistant Gram-negative pathogens. Structural optimization of polymyxins requires an in-depth understanding of its structure and how it relates to its antibacterial activity. Herein, the effect of hydrophobicity was explored by adding a secondary fatty acyl component of varying length onto the polymyxin structure at the amine side-chain of c-diaminobutyric acid at position 1, resulting to the development of dilipid polymyxins. The incorporation of an additional lipid was found to confer polymyxin activity against Gram-positive bacteria, to which polymyxins are inherently inactive against. The dilipid polymyxins showed selective antibacterial activity against Pseudomonas aeruginosa. Moreover, dilipid polymyxin 1 that consists of four carbon-long aliphatic lipids displayed the ability to enhance the antibacterial potency of other antibiotics in combination against P. aeruginosa, resembling the adjuvant activity of the well-known outer membrane permeabilizer polymyxin B nonapeptide (PMBN). Interestingly, our data revealed that dilipid polymyxin 1 and PMBN are substrates for the MexAB-OprM efflux system, and therefore are affected by efflux. In contrast, dilipid polymyxin analogs that consist of longer lipids and colistin were not affected by efflux, suggesting that the lipid component of polymyxin plays an important role in resisting active efflux. Our work described herein provides an understanding to the polymyxin structure that may be used to usher the development of enhanced polymyxin analogs.