4-硝基苯基 N-(苄氧羰基)-L-色氨酸酯 | 16624-64-9

• 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: 4-硝基苯基 N-(苄氧羰基)-L-色氨酸酯
• 中文别名: 4-硝基苯基N-(苄氧羰基)-L-色氨酸酯；N-苄氧羰基-L-色氨酸-p-硝基苯基脂
• 英文名称: α-carbobenzoxy-L-tryptophan p-nitrophenyl ester
• 英文别名: N-α-carbobenzoxy-L-tyrosine p-nitrophenyl ester；benzyloxycarbonyl-L-tryptophan p-nitrophenyl ester；benzyloxycarbonyltryptophan p-nitrophenyl ester；Z-L-Trp-ONp；Z-L-Trp-PNP；Z-Trp-ONp；(S)-4-Nitrophenyl 2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoate；(4-nitrophenyl) (2S)-3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 16624-64-9
• 化学式: C₂₅H₂₁N₃O₆
• mdl: MFCD00022758
• 分子量: 459.458
• InChiKey: MGXAOGDOJXOYRA-QHCPKHFHSA-N

物化性质

• 熔点：
  102-104 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 海关编码：
  2933990090
• 储存条件：
  室温、密封、干燥保存。

反应信息

• 作为反应物：
  描述：

  4-硝基苯基 N-(苄氧羰基)-L-色氨酸酯 在 γ-环糊精 作用下， 以 乙腈 为溶剂， 生成 N-苄氧羰基-L-色氨酸
  参考文献：
  名称：

  具有明显立体选择性的环糊精介导的氨基酸酯的脱酰作用。

  摘要：

  关于由α-，β-和γ-环糊精（CyDs）介导的ZD（L）-氨基酸酯（N-（苄氧基羰基）-D（L）-氨基酸对硝基苯酯）的水解（脱酰）作用，观察到Ala底物与γ-CyD脱酰基的对映选择性非常高（L / D = 9.0）。基于Michaelis-Menten原理的动力学结果表明，对映选择性应主要源自γ-CyD-底物（1：1）复合物形成后底物的脱酰基过程。还介绍了对包合物的计算机建模（分子力学）研究。

  DOI：

  10.1248/cpb.50.1283
• 作为产物：
  描述：

  对硝基苯酚 、 N-苄氧羰基-L-色氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以85%的产率得到4-硝基苯基 N-(苄氧羰基)-L-色氨酸酯
  参考文献：
  名称：

  Tryptophan-containing dipeptide derivatives as potent PPARγ antagonists: Design, synthesis, biological evaluation, and molecular modeling

  摘要：

  The discovery of peroxisome proliferator-activated receptor gamma (PPAR gamma) antagonists (also termed "selective PPAR gamma modulators, SPPAR gamma M") is now of a great interest in the treatment of diabetes and obesity. The structure of compound la (G3335, Fig. 1), a novel class of PPAR gamma antagonist, is entirely different from that of other reported PPAR gamma antagonists. A series of 35 novel analogues (1b-1, 9a-d, 13a-t) were designed, synthesized and evaluated against the agonistic effects exerted by rosiglitazone. These results indicated that most functional groups of la were conserved, and six new compounds (1b, 1c, and 9a-d) exhibited strong PPAR gamma antagonistic activities (IC50 values of 5.2-25.8 mu M) against 10 mu M rosiglitazone in the promotion of the PPAR gamma-LBD-CBP (ligand-binding domain and cAMP-response-element binding protein) interaction as investigated by yeast two-hybrid technology based assay. Molecular modeling studies for compounds 1a-d, 1h, 9c-d, and 13a were also presented. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.032

文献信息

• The role of the medium in solvent isotope effects on serine protease action
  作者：Jiaher Tian、Jue Tan、K Barbara Schowen、Richard L Schowen

  DOI：10.1139/v99-054

  日期：1999.6.1

  kcat(n) on n, the atom fraction of deuterium in the water component of the solvent) that are linear, regardless of the amount of acetonitrile in the medium. The isotope effect on kcat thus appears to arise from a single transition-state site and to be little affected by the medium. Contributions from the medium to solvent isotope effects on enzymic reactions clearly exist but appear not to be detectable in

  由 L-亮氨酸、L-苯丙氨酸和 L-色氨酸衍生的 N-碳苄氧基氨基酰基-Op-硝基苯基酯的水解，在牛胰腺 α-胰凝乳蛋白酶的催化下，pH 7.00，25.00°C，在含有 15.0% 至 60% 乙腈的水中% (v/v) 显示 kcat/Km 值随着水活度的 34 至 36 次幂而降低，并且 kcat 值基本恒定。溶剂同位素效应 kcat(H2O)/kcat(D2O) 范围从 2.1 到 3.0，质子库存（kcat(n) 对 n 的依赖性，溶剂的水组分中氘的原子分数）是线性的，与培养基中乙腈的量。因此，对 kcat 的同位素效应似乎来自单个过渡态位点，并且几乎不受介质影响。
• Synthesis and some pharmacological properties of [8-L-tryptophan]oxytocin
  作者：Miklos Bodanszky、John C. Tolle、Janny Seto、Wilbur H. Sawyer

  DOI：10.1021/jm00185a025

  日期：1980.11

  Condensation of (tert-butyloxycarbonyl)tocinoic acid with L-prolyl-L-tryptophylglycinamide produced the Boc derivative of a nonapeptide (disulfide) which on deprotection afforded [8-L-tryptophan]oxytocin. In assays on the rat uterus in vitro and in vivo the new analogue acts as both an agonist and an antagonist. The duration of both actions is prolonged.

  （叔丁氧羰基）环辛酸与L-脯氨酰基-L-色氨酸甘氨酰胺的缩合产生了九肽（二硫键）的Boc衍生物，其在脱保护后得到[8-L-色氨酸]催产素。在体外和体内大鼠子宫的测定中，新类似物既起激动剂作用又起拮抗剂作用。两项操作的持续时间都将延长。
• Structure-activity relationships of C-terminal tri- and tetrapeptide fragments that inhibit gastrin activity
  作者：Jean Martinez、Jean Pierre Bali、Richard Magous、Janine Laur、Marie Francoise Lignon、Christian Briet、Dino Nisato、Bertrand Castro

  DOI：10.1021/jm00381a002

  日期：1985.3

  A series of tri- and tetrapeptide derivatives, analogues of the gastrin C-terminal region with no phenylalanine residue, were synthesized. These peptides were tested for their ability to inhibit gastrin-stimulated acid secretion in vivo as well as binding of [125I]-(Nle11)-HG-13 to gastric mucosal cell receptors in vitro. Most of the peptides tested exhibited gastrin antagonist activity in vivo and in vitro. Most active derivatives were 20-30 times more potent than the well-known gastrin antagonist derivatives proglumide and benzotript and had 20-200 times more binding affinity. The smallest fragment exhibiting antagonist activity was the tripeptide Boc-L-tryptophyl-L-methionyl-L-aspartic acid amide.
• Ascenzi, Paolo; Sleiter, Giancarlo; Antonini, Eraldo, Gazzetta Chimica Italiana, 1982, vol. 112, # 7/8, p. 307 - 318
  作者：Ascenzi, Paolo、Sleiter, Giancarlo、Antonini, Eraldo

  DOI：——

  日期：——
• Ihara, Yasuji; Okamoto, Mari; Kawamura, Yoeko, Journal of the Chemical Society. Perkin transactions II, 1987, p. 607 - 612
  作者：Ihara, Yasuji、Okamoto, Mari、Kawamura, Yoeko、Nakanishi, Eiji、Nango, Mamoru、Koga, Joichi

  DOI：——

  日期：——