苄氧羰基-丁氧基谷氨酸-对硝基苯酯 | 7670-08-8

• 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
• 中文名称: 苄氧羰基-丁氧基谷氨酸-对硝基苯酯
• 英文名称: (benzyloxycarbonyl)-γ-tert-butyl-L-glutamic acid p-nitrophenyl ester
• 英文别名: Cbz-Glu(t-Bu)-ONp；Z-Glu(OBut)-ONp；Z-Glu(OtBu)-ONP；N-Benzyloxycarbonyl-L-glutaminsaeure-γ-tert.-butylester-α-(4-nitro-phenylester)；Benzyloxycarbonyl-glutaminsaeure-α-(4-nitro-phenylester)-γ-tert.-butylester；Benzyloxycarbonyl-γ-tert.-butyl-L-glutaminsaeure-p-nitrophenylester；5-O-tert-butyl 1-O-(4-nitrophenyl) (2S)-2-(phenylmethoxycarbonylamino)pentanedioate
• CAS: 7670-08-8
• 化学式: C₂₃H₂₆N₂O₈
• 分子量: 458.468
• InChiKey: QELUBUSZCPJCNC-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  苄氧羰基-丁氧基谷氨酸-对硝基苯酯 在 吡啶 作用下， 以 氯仿 为溶剂， 生成 Boc-Lys(Boc)-Glu(tBu)-Thr-OMe
  参考文献：
  名称：

  Scoffone,E. et al., Gazzetta Chimica Italiana, 1964, vol. 94, p. 743 - 759

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯酚 、 N-苄氧羰基-L-谷氨酸γ-叔丁酯 在 N,N'-二环己基碳二亚胺 作用下， 生成 苄氧羰基-丁氧基谷氨酸-对硝基苯酯
  参考文献：
  名称：

  多肽的研究。二十九。与牛胰核糖核酸酶A的N末端有关的合成肽（位置1-7）。

  摘要：

  DOI：

  10.1021/ja01081a039

文献信息

• A Synthesis of Human Proinsulin C-Peptide
  作者：Ken’ichi Igano、Yuriko Minotani、Nobuo Yoshida、Masao Kono、Ken Inouye

  DOI：10.1246/bcsj.54.3088

  日期：1981.10

  A peptide corresponding to the thirty-one amino acid sequence of human proinsulin C-peptide (positions 33–63 of proinsulin) was synthesized by the solid-phase method. The product was purified consecutively by gel filtration, DEAE-cellulose chromatography, and high-performance liquid chromatography (HPLC). The purified material behaved as a single component in reversed-phase HPLC, gave correct amino acid ratios, and was not distinguished from natural human C-peptide in terms of immunoreactivity and chromatographic behaviors. The α→β transpeptidation at the Asp-Leu sequence, possible to occur associated with the HF cleavage, was studied using model peptides to demonstrate that the formation of β-peptide was 3–4% regardless of whether the β-carboxylic acid is free or protected as a benzyl ester.

  一段对应于人类前胰岛素C肽（前胰岛素分子中的第33至63位氨基酸序列）的三十一个氨基酸序列的多肽通过固相法被合成。产物依次通过凝胶过滤、DEAE-纤维素色谱法和高性能液相色谱法（HPLC）进行纯化。纯化后的物质在反相HPLC中表现为单一组分，呈现出正确的氨基酸比例，并且在免疫反应性和色谱行为上与天然人C肽无法区分。关于与HF切割相关可能发生的Asp-Leu序列上的α→β转肽反应，通过模型肽的研究表明，无论β-羧酸是自由状态还是被保护为苄酯状态，β-肽的形成率都为3-4%。
• PEPTIDES WITH CYTOPROTECTIVE ACTIVITY
  申请人：Zamerton Holdings Limited

  公开号：EP2963052A2

  公开（公告）日：2016-01-06

  This invention is related to medicine and concerns peptides with cytoprotective activity selected from a group that includes Ac-Asp-Glu-OH, H-Asp-Glu-OCH3, H-Asp-Glu-NH - CH2-CH3, H-Val-Asp-Glu-OH, H-Leu-Asp- Glu-OH and H-Ala-Asp-Glu-Arg-OH, Ala-Asp-Glu, Lys-Asp-Glu and Asp-Glu-Gly, with the peptides remaining chemically stable in storage. Also proposed is a pharmaceutical composition containing effective quantities of peptides selected from a group that includes Ac-Asp-Glu-OH, H-Asp-Glu-OCH3, H-Asp-Glu-NH - CH2-CH3, H-Val-Asp-Glu-OH, H-Leu-Asp- Glu-OH and H-Ala-Asp-Glu-Arg-OH, Ala-Asp-Glu, Lys-Asp-Glu or Asp-Glu-Gly. The pronounced cytoprotective effect makes it possible to use the pharmaceutical composition in the food, cosmetological and pharmaceutical industries.

  这项发明涉及医学，涉及具有细胞保护活性的肽，所选肽包括Ac-Asp-Glu-OH、H-Asp-Glu-OCH3、H-Asp-Glu-NH-CH2-CH3、H-Val-Asp-Glu-OH、H-Leu-Asp-Glu-OH和H-Ala-Asp-Glu-Arg-OH、Ala-Asp-Glu、Lys-Asp-Glu和Asp-Glu-Gly，这些肽在储存中保持化学稳定。还提出了一种含有所选肽的药物组合物，该组合物包括Ac-Asp-Glu-OH、H-Asp-Glu-OCH3、H-Asp-Glu-NH-CH2-CH3、H-Val-Asp-Glu-OH、H-Leu-Asp-Glu-OH和H-Ala-Asp-Glu-Arg-OH、Ala-Asp-Glu、Lys-Asp-Glu或Asp-Glu-Gly。显著的细胞保护作用使得可以将该药物组合物用于食品、化妆品和制药行业。
• Development of Potent and Selective Phosphinic Peptide Inhibitors of Angiotensin-Converting Enzyme 2
  作者：Andreas Mores、Magdalini Matziari、Fabrice Beau、Philippe Cuniasse、Athanasios Yiotakis、Vincent Dive

  DOI：10.1021/jm701275z

  日期：2008.4.1

  Arimotensin-converting enzyme 2 (ACE2), a recently identified human homologue of angiotensin-converting enzyme, is a zinc metallocarboxypeptidase which may play a unique role in cardiovascular and renal function. Here we report the discovery of potent and selective inhibitors of ACE2, which have been identified by evaluating a series of phosphinic di- and tripeptides of the general formula: Z-Xaa(PO2-CH2)YaaOH and Ac-Zaa-Xaa(PO2-CH2)YaaOH. The most potent inhibitor in this series is a tripeptide that displays a K-i value of 0.4 nM toward ACE2 and is 3 orders of magnitude less potent toward carboxypeptidase A. Phosphinic tripeptides exhibit high potency exclusively when the Xaa position is occupied by a pseudoproline. A model of interaction between one inhibitor of this series and ACE2 suggests that the critical role played by a proline in inhibitors, but also for substrates hydrolysis, may rely on the presence of Tyr(510) in the ACE2 active site.
• Synthesis and biological activity of new peptide segments of gastrin exhibiting gastrin antagonist property
  作者：Jean Martinez、Richard Magous、Marie Francoise Lignon、Jeanine Laur、Bertrand Castro、Jean Pierre Bali

  DOI：10.1021/jm00378a012

  日期：1984.12

  A series of C-terminal peptide segments of gastrin, i.e., (tert-butyloxycarbonyl)-L-tryptophyl-L-methionyl-L-aspartic acid amide, (tert-butyloxycarbonyl)-glycyl-L-tryptophyl-L-methionyl-L-aspartic acid amide, (tert-butyloxy-carbonyl)-L-tyrosyl-glycyl-L-tryptophyl-L-methionyl-L-asp artic acid amide, and (benzyloxycarbonyl)-L-glutamyl-L-alanyl-L-tyrosyl-glycyl-L-tryptophyl-L -methionyl-L-aspartic acid amide were prepared and were shown to competitively inhibit the binding of labeled human gastrin to its receptors in an isolated gastric mucosal cell preparation and to antagonize the action of gastrin on gastric acid secretion (ED50 from 1.5 to 7 mg/kg) in vivo in the reperfused rat stomach, determined according to the method of Ghosh and Schild. From these studies, it could be concluded that the C-terminal phenylalanine residue, which is of primary importance for intrinsic biological gastrin-like activity, is not essential for binding to gastrin receptors.
• Studies on Polypeptides. XXIX. Synthetic Peptides Related to the N-Terminus of Bovine Pancreatic Ribonuclease A (Positions 1-7)^1-4
  作者：Klaus Hofmann、Ralph Schmiechen、Robert D. Wells、Yecheskel Wolman、Noboru Yanaihara

  DOI：10.1021/ja01081a039

  日期：1965.2