(4S)-5-氨基-4-[[芴甲氧羰基]氨基]-5-氧代戊酸 | 288149-55-3

• 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
• 中文名称: (4S)-5-氨基-4-[[芴甲氧羰基]氨基]-5-氧代戊酸
• 英文名称: Fmoc-iso-Gln-OH
• 英文别名: Fmoc-D-iso-Gln-OH；Fmoc-D-isoglutamine；Fmoc-D-Glu-NH2；(S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-amino-5-oxopentanoic acid；(4S)-5-amino-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid
• CAS: 288149-55-3
• 化学式: C₂₀H₂₀N₂O₅
• 分子量: 368.389
• InChiKey: MZRFDZFXTSDMFA-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  5

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：

  L-丙氨酸 、 Fmoc-L-缬氨酸 、 (4S)-5-氨基-4-[[芴甲氧羰基]氨基]-5-氧代戊酸 、 棕榈酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 4-二甲氨基吡啶 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 palmitoyl-VVVAAAEEE-NH2
  参考文献：
  名称：

  Pathway Selection in Peptide Amphiphile Assembly

  摘要：

  The nature of supramolecular structures could be strongly affected by the pathways followed during their formation just as mechanisms and final outcomes in chemical reactions vary with the conditions selected. So far this is a largely unexplored area of supramolecular chemistry. We demonstrate here how different preparation protocols to self-assemble peptide amphiphiles in water can result in the formation of different supramolecular morphologies, either long filaments containing β-sheets or smaller aggregrates containing peptide segments in random coil conformation. We found that the assembly rate into β-sheets decreases in the presence of a destabilizing "good" solvent like hexafluoroisopropanol (HFIP) and is affected by transient conditions in solution. Also the peptide amphiphile investigated spontaneously nucleates the β-sheet-containing filaments at a critical fraction of HFIP in water below 21%. Furthermore, β-sheet assemblies have a high kinetic stability and, once formed, do not disassemble rapidly. We foresee that insights into the characteristic dynamics of a supramolecular system provide an efficient approach to select the optimum assembly pathway necessary for function.

  DOI：

  10.1021/ja503882s

文献信息

• V1A RECEPTOR AGONISTS
  申请人：FERRING B.V.

  公开号：US20160122386A1

  公开（公告）日：2016-05-05

  Compounds of formula (I), salts thereof, and compositions and uses thereof are described. The compounds are useful as V1a vasopressin agonists, for the treatment of, e.g., complications of cirrhosis, including bacterial peritonitis, HRS2 and refractory ascites.

  公式（I）的化合物，其盐，以及其组合物和用途被描述。这些化合物可用作V1a加压素激动剂，用于治疗，例如，肝硬化并发症，包括细菌性腹膜炎，HRS2和难治性腹水。
• Salutaxel, a Conjugate of Docetaxel and a Muramyl Dipeptide (MDP) Analogue, Acts as Multifunctional Prodrug That Inhibits Tumor Growth and Metastasis
  作者：Xiaoming Wen、Purong Zheng、Yao Ma、Yingye Ou、Weixin Huang、Shuo Li、Shoujia Liu、Xuan Zhang、Ziyu Wang、Qianli Zhang、Wenming Cheng、Ruwen Lin、Hongzu Li、Youyou Cai、Chunyun Hu、Ningbin Wu、Long Wan、Tingting Pan、Jinlong Rao、Xuelu Bei、Weibin Wu、Jian Jin、Jie Yan、Gang Liu

  DOI：10.1021/acs.jmedchem.7b01407

  日期：2018.2.22

  Salutaxel (3) is a conjugate of docetaxel (7) and a muramyl dipeptide (MDP) analogue. Docetaxel (7) has been recognized as a highly active chemotherapeutic agent against various cancers. MDP and its analogues are powerful potentiators of the antitumor actions of various tumor-necrotizing agents. This article documents the discovery of compound 3 and presents pharmacological proof of its biological function in tumor-bearing mice. Drug candidate 3 was superior to compound 7 in its ability to prevent tumor growth and metastasis. Compound 3 suppressed myeloid-derived suppressor cell (MDSC) accumulation in the spleens of tumor-bearing mice and decreased various serum inflammatory cytokines levels. Furthermore, compound 3 antagonized the nucleotide-binding oligomerization domain-like receptor 1 (NOD1) signaling pathway both in vitro and in vivo.
• Discovery of 1,4-Benzodiazepine-2,5-dione (BZD) Derivatives as Dual Nucleotide Binding Oligomerization Domain Containing 1/2 (NOD1/NOD2) Antagonists Sensitizing Paclitaxel (PTX) To Suppress Lewis Lung Carcinoma (LLC) Growth in Vivo
  作者：Suhua Wang、Jingshu Yang、Xueyuan Li、Zijie Liu、Youzhen Wu、Guangxu Si、Yiran Tao、Nan Zhao、Xiao Hu、Yao Ma、Gang Liu

  DOI：10.1021/acs.jmedchem.7b00608

  日期：2017.6.22

  Nucleotide-binding oligomerization domain-like receptors (NLRs) are intracellular sensors of pathogen-associated molecular patterns (PAMPs) and damage-associated molecular patterns (DAMPs). Previously, we reported nucleotide-binding oligomerization domain-containing protein 1 (NOD1) antagonists (II, 12) and a NOD2 antagonist (9) that sensitized docetaxel (DTX) or paclitaxel (PTX) treatment for breast or lung cancer. In this article, we describe for the first time a 1,4-benzodiazepine-2,5-dione (BZD) derivative (26bh) that acts as a dual NOD1/NOD2 antagonist and inhibits both nuclear factor kappa B (NF-kappa B) and mitogen-activated protein kinase (MAPK) inflammatory signaling, thereby sensitizing PTX to suppress Lewis lung carcinoma (LLC) growth. After investigation of the compound's cytotoxicity, a systematic structure-activity relationship (SAR) was completed and revealed several key factors that were necessary to maintain antagonistic ability. This study establishes the possibility for using adjuvant treatment to combat cancer by antagonizing both NOD1 and NOD2 signaling.
• Pathway Selection in Peptide Amphiphile Assembly
  作者：Peter A. Korevaar、Christina J. Newcomb、E. W. Meijer、Samuel I. Stupp

  DOI：10.1021/ja503882s

  日期：2014.6.18

  The nature of supramolecular structures could be strongly affected by the pathways followed during their formation just as mechanisms and final outcomes in chemical reactions vary with the conditions selected. So far this is a largely unexplored area of supramolecular chemistry. We demonstrate here how different preparation protocols to self-assemble peptide amphiphiles in water can result in the formation of different supramolecular morphologies, either long filaments containing β-sheets or smaller aggregrates containing peptide segments in random coil conformation. We found that the assembly rate into β-sheets decreases in the presence of a destabilizing "good" solvent like hexafluoroisopropanol (HFIP) and is affected by transient conditions in solution. Also the peptide amphiphile investigated spontaneously nucleates the β-sheet-containing filaments at a critical fraction of HFIP in water below 21%. Furthermore, β-sheet assemblies have a high kinetic stability and, once formed, do not disassemble rapidly. We foresee that insights into the characteristic dynamics of a supramolecular system provide an efficient approach to select the optimum assembly pathway necessary for function.
• FIBRONECTIN ADHESION INHIBITORS
  申请人：ZENECA LIMITED

  公开号：EP0800535A1

  公开（公告）日：1997-10-15