4-硝基苯基N-{[(2-甲基-2-丙基)氧基]羰基}-L-酪氨酸酯 | 20866-55-1

• 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-{[(2-甲基-2-丙基)氧基]羰基}-L-酪氨酸酯
• 英文名称: N-(tert-butyloxycarbonyl)-L-tyrosine, 4-nitrophenol ester
• 英文别名: Boc-Tyr-ONp；(4-nitrophenyl) (2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 20866-55-1
• 化学式: C₂₀H₂₂N₂O₇
• mdl: MFCD00076991
• 分子量: 402.404
• InChiKey: BNBKZMYOTFMWHX-KRWDZBQOSA-N

物化性质

• 沸点：
  604.3±55.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  4-硝基苯基N-{[(2-甲基-2-丙基)氧基]羰基}-L-酪氨酸酯 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Methyltrypsin-Catalyzed Peptide Coupling: Comparison of Alkyl Ester and Guanidinophenyl Ester Derivatives as Acyl Donor Component

  摘要：

  Methyltrypsin-catalyzed peptide synthesis has been studied by using conventional alkyl ester and p-guanidinophenyl ester derivatives of alpha-amino acid as the acyl donor component. They were found to be coupled with alpha-amino acid derivatives (acyl acceptor component) to produce dipeptide. The behavior of methyltrypsin toward both the substrates has been studied. (C) 1997 Academic Press.

  DOI：

  10.1006/bioo.1997.1076
• 作为产物：
  描述：

  对硝基苯酚 、 Boc-L-酪氨酸 在 N-甲基吗啉 、 N,N'-二异丙基碳二亚胺 作用下， 以 氯仿 为溶剂， 生成 4-硝基苯基N-{[(2-甲基-2-丙基)氧基]羰基}-L-酪氨酸酯
  参考文献：
  名称：

  Himaja; Desai, Siddharth; Sambanthan, A. Thirugnana, Asian Journal of Chemistry, 2010, vol. 22, # 4, p. 2914 - 2918

  摘要：

  DOI：

文献信息

• On the use of carboxamidomethyl esters (cam esters) in the synthesis of model peptides. scope and limitations
  作者：Jean Martinez、Janine Laur、Bertrand Castro

  DOI：10.1016/s0040-4020(01)96451-8

  日期：1985.1

  protecting group for peptide synthesis was demonstrated. The synthesis of the chemotactic peptide For-Met-Leu-Phe-OH as well as the synthesis of Met-enkephalin using CAM ester as carboxyl terminal protection were performed. These esters showed good stability during acidolytic removal of BOC N-protecting group, during hydrogenolysis of Z N-protecting group and during removal of FMOC N-protecting group. CAM

  证明了羧酰胺基甲基酯（CAM酯）作为用于肽合成的羧基保护基的用途。进行了趋化肽For-Met-Leu-Phe-OH的合成以及使用CAM酯作为羧基末端保护的Met-脑啡肽的合成。这些酯在酸解去除BOC N-保护基期间，Z N-保护基的氢解期间和FMOC N-保护基的去除期间显示出良好的稳定性。CAM酯可被NaOH 0.5 N或Na 2 CO 3迅速裂解。但是，当序列中存在天冬氨酸的β-苄基酯时，我们未能成功地选择性除去CAM酯。
• Esters of L-Dopa: Structure-hydrolysis Relationships and Ability to Induce Circling Behaviour in an Experimental Model of Hemiparkinsonism
  作者：Michele Brunner-Guenat、Pierre-Alain Carrupt、Giuseppe Lisa、Bernard Testa、Sarah Rose、Kerrie Thomas、Peter Jenner、Paolo Ventura

  DOI：10.1111/j.2042-7158.1995.tb05755.x

  日期：2011.4.12

  A number of carboxylate esters of L-dopa, some of which are novel, were examined for their physicochemical and biological properties. A few esters of tyrosine and phenylalanine were included for comparison.

  The compounds displayed great differences in their lipophilicity and stability towards chemical and enzymatic (human plasma) hydrolysis. Within subseries, relationships exist between structural properties and rate constants of chemical or enzymatic hydrolysis. In an experimental model of hemiparkinsonism (circling behaviour in rats), some of the L-dopa esters (the isopropyl, sec-butyl and 2-(tetrahydropyr-anyl)methyl esters) showed an activity distinctly greater than that of L-dopa, although the difference was not statistically significant.

  摘要：对多种L-多巴酸羧酯进行了研究，其中一些是新颖的，检测了它们的理化性质和生物学特性。为了比较，还包括了一些酪氨酸和苯丙氨酸的酯。这些化合物在脂溶性和对化学和酶解（人类血浆）的稳定性方面存在很大差异。在亚系列中，结构性质与化学或酶解速率常数之间存在关系。在实验性半帕金森氏症模型（大鼠的旋转行为）中，一些L-多巴酸酯（异丙基、丙基和2-（四氢吡喃基）甲酯）显示出明显高于L-多巴酸的活性，尽管差异并不具有统计学意义。
• Alpha-aminoamide derivatives as melanocortin agonists
  申请人：——

  公开号：US20030232807A1

  公开（公告）日：2003-12-18

  Novel piperazine and homopiperazine derivatives are agonists of melanocortin receptor(s) and are useful for the treatment, control, or prevention of diseases and disorders responsive to the activation of the melanocortin receptors. The compounds of the present invention are therefore useful for treatment or prevention of diseases and disorders such as obesity, diabetes, and sexual dysfunction.

  新型哌嗪和异哌嗪衍生物是黑色素皮质激素受体的激动剂，并可用于治疗、控制或预防对黑色素皮质激素受体激活敏感的疾病和紊乱。因此，本发明的化合物可用于治疗或预防肥胖、糖尿病和性功能障碍等疾病和紊乱。
• 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.
• LIPKOWSKI, ANDRZEJ W.
  作者：LIPKOWSKI, ANDRZEJ W.

  DOI：——

  日期：——