H-Glu(OBzl)-NH₂ | 80064-48-8

• 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: H-Glu(OBzl)-NH₂
• 英文别名: Isoglutamine benzyl ester；benzyl (4S)-4,5-diamino-5-oxopentanoate
• CAS: 80064-48-8
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: RHKPFPFNUDBBOM-JTQLQIEISA-N

物化性质

• 沸点：
  446.3±45.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  H-Glu(OBzl)-NH₂ 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 87.0h， 生成 Boc-Glu-Glu-Glu-Glu-NH₂
  参考文献：
  名称：

  Oligo-Asp Tag/Zn(II) 复合探针作为蛋白质标记和荧光成像的新对

  摘要：

  为了在复杂的生物系统中完成对特定蛋白质的选择性标记，需要掺入蛋白质中的肽标签和互补的小分子探针。尽管已经开发了多种肽标签/探针对作为蛋白质分析的分子工具，但适用于蛋白质实时成像的对的可用性仍然有限。我们现在报告了一个新的肽标签/人工探针对，由可遗传编码的低聚天冬氨酸序列（D4 标签，(D4)n，n = 1-3）和相应的多核 Zn(II) 复合物 (Zn(II)- DpaTyrs）。Zn(II)-DpaTyr 探针与 D4 标签的强结合亲和力是多重配位键和多价效应的结果。用等温滴定量热法定量测定。

  DOI：

  10.1021/ja0618604
• 作为产物：
  描述：

  (S)-2-(4-Methoxy-benzyloxycarbonylamino)-pentanedioic acid 5-benzyl ester 1-(4-nitro-phenyl) ester 在 ammonium hydroxide 、 苯甲醚 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 H-Glu(OBzl)-NH₂
  参考文献：
  名称：

  Studies on peptides. CXX. Synthesis of growth hormone releasing factor (GRF-37-NH2) and N.ALPHA.-biotinyl-GRF-44-NH2.

  摘要：

  与人胰腺肿瘤衍生肽之一（称为生长激素释放因子（hpGRF））的完整氨基酸序列相对应的七十三肽的酰胺形式是使用苯硫基苯甲醚介导的脱保护程序以常规方式合成的。在体内测定中，该肽 (hpGRF-37-NH2) 与合成的四十四肽酰胺 (hpGRF-44-NH2) 具有相同的活性。然而，在体外测定中，合成的hpGRF-37-NH2的效力仅为合成的hpGRF-44-NH2的15%。此外，还制备了 Nα-生物素-GRF-44-NH2 用于组织化学受体研究。该 GRF 衍生物的活性约为 hpGRF-44-NH2 的 60%。

  DOI：

  10.1248/cpb.32.1200

文献信息

• HUMAN GLUCAGON-LIKE-PEPTIDE-1 MODULATORS AND THEIR USE IN THE TREATMENT OF DIABETES RELATED CONDITIONS
  申请人：Haque Shamsul Tasir

  公开号：US20070238669A1

  公开（公告）日：2007-10-11

  The present invention provides novel human glucagon-like peptide-1 (GLP-1)-receptor modulators that have biological activity similar or superior to native GLP-1 peptide and thus are useful for the treatment or prevention of diseases or disorders associated with GLP activity. Further, the present invention provides novel, chemically modified compounds that not only stimulate insulin secretion in type II diabetics, but also produce other beneficial insulinotropic responses. These synthetic peptide GLP-1 receptor modulators exhibit increased stability to proteolytic cleavage making them ideal therapeutic candidates for oral or parenteral administration. The compounds of this invention show desirable pharmacokinetic properties and desirable potency in efficacy models of diabetes.

  本发明提供了新型人类胰高血糖素样肽-1（GLP-1）受体调节剂，其生物活性类似或优于天然GLP-1肽，因此可用于治疗或预防与GLP活性相关的疾病或障碍。此外，本发明提供了新的化学修饰化合物，不仅可以刺激2型糖尿病患者的胰岛素分泌，还可以产生其他有益的胰岛素促进反应。这些合成肽GLP-1受体调节剂表现出对蛋白酶水解的稳定性增加，使它们成为口服或静脉注射理想的治疗候选药物。本发明的化合物在糖尿病疗效模型中表现出理想的药代动力学特性和理想的效力。
• DIPEPTIDE MIMETICS OF NGF AND BDNF NEUROTROPHINS
  申请人：Federal State Budgetary Institution "Research Zakusov Institute of Pharmacology"

  公开号：EP2397488B1

  公开（公告）日：2019-03-27
• Structure activity studies on the C-terminal hexapeptide of substance P with modifications at the glutaminyl and methioninyl residues
  作者：Constantine Poulos、George Stavropoulos、John R. Brown、Christopher C. Jordan

  DOI：10.1021/jm00391a041

  日期：1987.8

  Analogues of [Orn6]-SP6-11 have been synthesized in which the SCH3 group of the Met11 side chain is replaced by other functional groups, such as (CH2)2NH2, COOH, CONH2, and COOR, which have basic, acid, or neutral character and which may act as either H-bonding donors or H-bonding acceptors. These analogues were tested in guinea pig ileum and rat colon muscularis mucosae, in vitro. Substitution of Lys, Gln, or Glu at position 11 caused a marked reduction in biological activity in both tissues. In contrast, the glutamate benzyl ester analogue had only slightly reduced activity in the guinea pig ileum and an increased (4.7 times) activity in the rat colon. It is concluded that charged groups in the side chain at position 11 of SP6-11 reduce the biological activity of SP hexapeptide.
• Conformationally flexible platelet aggregation inhibitors based on the tetrapeptide Arg-Gly-Asp-Arg
  作者：SI Klein、M Czekaj、BF Molino、V Chu

  DOI：10.1016/s0223-5234(99)80069-5

  日期：1997.10

  A series of nonpeptide fibrinogen receptor antagonists based upon the tetrapeptide Arg-Gly-Asp-Arg were prepared. These relatively simple derivatives incorporate a high degree of conformational flexibility that was anticipated to allow them to attain the requisite conformation for binding to the platelet fibrinogen receptor. Optimization of the distances between the required acidic and basic functional groups led eventually to compound 7, which is a one hundred-fold more potent inhibitor of platelet aggregation than the peptide it is based upon.
• Synthesis of biologically active biotinylated muramyl dipeptides
  作者：Catherine Leimkuhler Grimes、Daniel K. Podolsky、Erin K. O’Shea

  DOI：10.1016/j.bmcl.2010.08.056

  日期：2010.10

  Muramyl dipeptide (MDP) is believed to interact with an innate immune receptor, Nod2. To identify the cellular receptor for MDP, we have synthesized biotinylated MDP isomers and tested the ability of these compounds to activate Nod2 in a cell-based assay. We found that the modification of MDP does not perturb its ability to activate Nod2. These tagged versions of MDP will be useful to identify the cellular receptor of the immunostimulatory molecules. (c) 2010 Elsevier Ltd. All rights reserved.