Z-Val-Gly-OBu^t | 19653-58-8

• 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: Z-Val-Gly-OBu^t
• 英文别名: (S)-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)acetate；tert-butyl N-(N-(benzyloxycarbonyl)-L-valyl)glycinate；Cbz-Val-Gly-OtBu；N-Benzyloxycarbonyl-valylglycin-tert.-butylester；tert-butyl 2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]acetate
• CAS: 19653-58-8
• 化学式: C₁₉H₂₈N₂O₅
• 分子量: 364.442
• InChiKey: KXCZHZRHWUHYBK-INIZCTEOSA-N

物化性质

• 熔点：
  90-91 °C
• 沸点：
  525.8±40.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Val-Gly-OBu^t 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 N-甲基吗啉盐酸盐 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， -10.0~25.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 Cbz-Tyr-D-Ala-Phe-Asp(OtBu)-Val-Val-Gly-OtBu
  参考文献：
  名称：

  Unique sequence in deltorphin C confers structural requirement for δ opioid receptor selectivity

  摘要：

  A series of deltorphin C (H-Tyr-D-Ala-Phe-Asp-Val-Val-Gly-NH2) analogues were synthesized to assess the consequences of changing anionic and hydrophobic residues on delta receptor selectivity. Analogues with altered C-terminal groups, inverted sequences, or esterified with tert-butyl, benzyl, or ethyl groups revealed that high delta selectivity required an unmodified amino acid sequence. Shifts of Asp and hydrophobic residues decreased delta selectivity due to loss in delta affinity (5- to almost-equal-to 700-fold); mu affinity was unchanged or increased 14-fold. Suppression of charge or deamidation diminished delta selectivity through reduced delta and modified mu affinities. Data provide evidence that a negative charge does not a priori guarantee high selectivity and specific alignment of anionic and hydrophobic residues might facilitate optimum spatial configuration which complements the 8 receptor binding site.

  DOI：

  10.1016/0223-5234(92)90113-f
• 作为产物：
  描述：

  2-甲基-2-丙基N-[(苄氧基)羰基]甘氨酸酯 在 钯 氢气 、 N,N'-二环己基碳二亚胺 、 HONB 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 Z-Val-Gly-OBu^t
  参考文献：
  名称：

  Wakimasu, Mitsuhiro; Kitada, Chieko; Fujino, Masahiko, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 8, p. 2766 - 2779

  摘要：

  DOI：

文献信息

• 2-Oxoamides based on dipeptides as selective calcium-independent phospholipase A 2 inhibitors
  作者：Anneta Smyrniotou、Maroula G. Kokotou、Varnavas D. Mouchlis、Efrosini Barbayianni、George Kokotos、Edward A. Dennis、Violetta Constantinou-Kokotou

  DOI：10.1016/j.bmc.2016.12.007

  日期：2017.2

  of synthetic compounds (bromoenol lactone and polyfluoroketones). To expand the chemical diversity, a variety of 2-oxoamides based on dipeptides and ether dipeptides were synthesized and studied for their in vitro inhibitory activity on human GVIA iPLA2 and their selectivity over the other major intracellular GIVA cPLA2 and the secreted GV sPLA2. Structure-activity relationship studies revealed the

  不依赖钙的磷脂酶A 2（GVIA iPLA 2）最近引起了人们的关注，将其作为药物靶标。已知的GVIA iPLA 2抑制剂的数量仅限于少数几种合成化合物（溴烯醇内酯和多氟酮）。为了扩大化学多样性，合成了多种基于二肽和醚二肽的2-氧酰胺，并研究了它们对人GVIA iPLA 2的体外抑制活性以及对其他主要细胞内GIVA cPLA 2和分泌的GV sPLA 2的选择性。。结构-活性关系研究表明，第一个2-氧代酰胺衍生物（GK317）对GVIA iPLA 2（X I（50）值为0.007），同时相对于GIVA cPLA 2和GV sPLA 2具有显着的选择性。
• Single Electron Transfer‐Induced Selective α‐Oxygenation of Glycine Derivatives
  作者：Navyasree Venugopal、Johannes Moser、Margaréta Vojtíčková、Ivana Císařová、Burkhard König、Ullrich Jahn

  DOI：10.1002/adsc.202100964

  日期：2022.1.18

  combination provides stable alkoxyamines in good to excellent yields. The methodology is expanded to glycine-containing dipeptides demonstrating selective oxygenation at the glycine unit. The orthogonal reactivity potential of oxygenated glycines for transformation to other amino acid derivatives is explored.

  氨基酸的修饰是有机和生物有机化学中的重要策略。与常见的侧链功能化相比，对主链修饰的探索要少得多。尤其是甘氨酸单元似乎很有吸引力且用途广泛，因为可以潜在地引入广泛的功能。我们在此报告稳定且能够进一步功能化的甘氨酸盐的氧化修饰。通过 TEMPO 或 FeCp 2 PF 6选择性氧化甘氨酸烯醇化物/TEMPO 试剂组合以良好至优异的产率提供稳定的烷氧基胺。该方法扩展到含甘氨酸的二肽，在甘氨酸单元显示选择性氧合。探索了氧化甘氨酸转化为其他氨基酸衍生物的正交反应潜力。
• Synthesis of<i>N</i>-Terminal Nonapeptide of Trypsinogen and Its Hydrolysis by Trypsin
  作者：Norio Yoshida、Tetsuo Kato、Nobuo Izumiya

  DOI：10.1246/bcsj.43.2912

  日期：1970.9

  An N-terminal nonapeptide fragment of bovine trypsinogen, H-l-Val-l-Asp-l-Asp-l-Asp-l-Asp-l-Lys-l-Ile-l-Val-Gly-OH, was synthesized via two routes and its susceptibility with trypsin was investigated. Protected derivatives, t-butyloxycarbonyl protected nonapeptide t-butyl ester and benzyloxycarbonyl protected nonapeptide benzyl ester, were prepared by stepwise elongation. Removal of the protecting groups was carried out by treatment with trifluoroacetic acid and hydro-genation respectively. The naked peptide was purified with chromatography on ECTEOLA cellulose column using dilute acetic acid as a solvent. Upon lyophilization the desired nonapeptide was obtained as colorless powder, a portion of the product being digested with trypsin. Rate of tryptic hydrolysis of the peptide was found to be unexpectedly low in the absence of calcium ion, while considerable acceleration of the hydrolysis by calcium ion was noted.

  一种牛胰蛋白酶原的N-末端九肽片段H-l-Val-l-Asp-l-Asp-l-Asp-l-Asp-l-Lys-l-Ile-l-Val-Gly-OH通过两条途径合成，并研究了其与胰蛋白酶的敏感性。通过逐步延伸的方法制备了保护性衍生物，分别为t-丁氧羰基保护的九肽t-丁酯和苄氧羰基保护的九肽苄酯。去除保护基团是通过分别用三氟乙酸和氢化处理进行的。裸肽通过在ECTEOLA纤维素柱上用稀醋酸作为溶剂的色谱法进行纯化。冷冻干燥后，获取了无色粉末的目标九肽，部分产品与胰蛋白酶消化。发现在缺乏钙离子的情况下，肽的胰蛋白酶水解速率意外地较低，而发现钙离子显著加速了其水解。
• Savrda; Bricas, Bulletin de la Societe Chimique de France, 1968, vol. 6, p. 2423 - 2429
  作者：Savrda、Bricas

  DOI：——

  日期：——
• 2-Oxoamide inhibitors of phospholipase A2 activity and cellular arachidonate release based on dipeptides and pseudodipeptides
  作者：Efrosini Barbayianni、Daren Stephens、Andrej Grkovich、Victoria Magrioti、Yuan-Hao Hsu、Panagiotis Dolatzas、Dimitrios Kalogiannidis、Edward A. Dennis、George Kokotos

  DOI：10.1016/j.bmc.2009.03.069

  日期：2009.7

  A series of 2-oxoamides based on dipeptides and pseudodipeptides were synthesized and their activities towards two human intracellular phospholipases A(2) (GIVA cPLA(2) and GVIA iPLA(2)) and one human secretory phospholipase A(2) (GV sPLA(2)) were evaluated. Derivatives containing a free carboxyl group are selective GIVA cPLA(2) inhibitors. A derivative based on the ethyl ester of an ether pseudodipeptide is the first 2-oxoamide, which preferentially inhibits GVIA iPLA2. The effect of 2-oxoamides on the generation of arachidonic acid from RAW 264.7 macrophages was also studied and it was found that selective GIVA cPLA(2) inhibitors preferentially inhibited cellular arachidonic acid release; one pseudodipeptide gave an IC50 value of 2 mu M. (C) 2009 Elsevier Ltd. All rights reserved.