Boc-Ile-O-COOEt | 98807-42-2

• 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: Boc-Ile-O-COOEt
• CAS: 98807-42-2
• 化学式: C₁₄H₂₅NO₆
• 分子量: 303.356
• InChiKey: XDARYFQVHKKSSD-UWVGGRQHSA-N

物化性质

• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Boc-Ile-O-COOEt 在 辛酸铑 lithium hydroxide 、 ammonium hydroxide 、 巯基乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 (S,S)-ethyl 2-(1-tert-butoxycarbonylamino-2-methyl-butyl)-5-(indol-3-yl)oxazole-4-carboxylate
  参考文献：
  名称：

  Dirhodium（II）催化的3-吲哚基重氮酮酸酯反应中竞争性NH插入和Wolff重排的控制。海洋5-（3-吲哚基）恶唑Martefragin A的潜在前体的合成。

  摘要：

  在己酰胺的存在下，吡啶鎓（II）催化的3-吲哚基α-重氮-β-酮酸酯25的反应导致竞争的金属卡宾NH插入和Wolff重排。另一方面，相应的苯基重氮酮酸酯32仅给出NH插入的产物，这表明吲哚部分更倾向于1，2-重排。的竞争过程的范围内的3-吲哚基α重氮基β酮酯（进行了调查36，38，40，44）; 这些研究表明，吲哚氮上存在强的吸电子基团可以有效地抑制沃尔夫重排。铱（II）催化剂在促进插入过程方面也比铜或路易斯酸催化剂更有效。N-H插入产物，所述酮酰胺（26，47，49，51，53），进行脱水闭环容易成相应的5-（3-吲哚基）恶唑。NH插入/环脱水方法用于海洋天然产物martefragin A的正式合成中。因此，N -Boc高异亮氨酸酰胺23通过对脱氢氨基酸进行不对称氢化制备，用衍生自N- nosyl吲哚基重氮酯40的铑卡宾进行NH插入，然后进行环化脱水和脱保护，得到5-（3-吲哚基）恶唑玛替fragin

  DOI：

  10.1021/jo050303h
• 作为产物：
  描述：

  BOC-L-异亮氨酸 、 焦碳酸二乙酯 在 N-甲基吡咯烷酮 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Boc-Ile-O-COOEt
  参考文献：
  名称：

  Chen, Francis M. F.; Benoiton, N. Leo, Canadian Journal of Chemistry, 1987, vol. 65, p. 619 - 625

  摘要：

  DOI：

文献信息

• Peptidomimetics Through Click Chemistry: Synthesis of Novel β-Keto Triazole Acids from N-Protected Amino Acids
  作者：N. Narendra、T. M. Vishwanatha、Vommina V. Sureshbabu

  DOI：10.1007/s10989-010-9214-z

  日期：2010.12

  An efficient procedure for the preparation of azidomethylketones from N-urethane protected amino acids and their application in Cu(I) catalyzed azide-alkyne cycloaddition reaction are described. The synthesis has been carried out under mild conditions with all the commonly used urethane protected (Fmoc, Boc and Z) amino acids and the desired azides/triazoles were obtained in good yields. Incorporation of these triazole amino acids into small peptides generating dipeptidomimetics containing β-keto triazole units has also been demonstrated.

  描述了一种有效的程序，用于从N-氨基甲酸酯保护的氨基酸制备叠氮甲基酮及其在铜(I)催化的叠氮-炔烃环加成反应中的应用。该合成在温和条件下进行，适用于所有常用的氨基甲酸酯保护的氨基酸（Fmoc、Boc 和 Z），并以良好的产率获得了所需的叠氮化物/三唑化物。还展示了将这些三唑氨基酸纳入小肽中，生成含有β-酮三唑单元的二肽模仿物。
• CuI-Promoted One-Pot Synthesis of N-Boc Protected β-Ketotriazole Amino Acids: Application in the Synthesis of New Class of Dipeptidomimetics
  作者：T. M. Vishwanatha、N. Narendra、Vommina V. Sureshbabu

  DOI：10.2174/092986612799363172

  日期：2012.3.1

  One-pot click chemistry of Nα-Boc-bromomethylketones, NaN3 and propiolic acid affords N-Boc protected 1,4- disubstituted 1,2,3-β-ketotriazole acids in good to excellent yield. The use of CuI as catalyst and DMSO as solvent leads the click reaction to efficient, practical and column-free preparation of the title compounds. The utility of the resulting unnatural amino acids as building blocks to prepare triazole possessing peptidomimetics is also delineated.

  Nα-Boc-溴甲基酮、NaN3和丙炔酸的一锅点击化学反应以良好至优异的产率提供了N-Boc保护的1,4-二取代1,2,3-β-酮三唑酸。使用CuI作为催化剂和DMSO作为溶剂使得点击反应变得高效、实用且无需柱层析即可制备标题化合物。还阐述了所得非天然氨基酸作为构建模块制备含三唑的类肽的实用性。
• Isolation and synthesis of falcitidin, a novel myxobacterial-derived acyltetrapeptide with activity against the malaria target falcipain-2
  作者：Brinda Somanadhan、Santosh R Kotturi、Chung Yan Leong、Robert P Glover、Yicun Huang、Horst Flotow、Antony D Buss、Martin J Lear、Mark S Butler

  DOI：10.1038/ja.2012.123

  日期：2013.5

  A 384-well microtitre plate fluorescence cleavage assay was developed to identify inhibitors of the cysteine protease falcipain-2, an important antimalarial drug target. Bioassay-guided isolation of a MeOH extract from a myxobacterium Chitinophaga sp. Y23 isolated from soil collected in Singapore, led to the identification of a new acyltetrapeptide, falcitidin (1), which displayed an IC50 value of 6 μM against falcipain-2. The planar structure of 1 was secured by NMR and MS/MS analysis. Attempts to isolate further material for biological testing were hampered by inconsistent production and by a low yield (<100 μg l−1). The absolute configuration of 1 was determined by Marfey’s analysis and the structure was confirmed through total synthesis as isovaleric acid-D-His-L-Ile-L-Val-L-Pro-NH2. Falcitidin (1) is the first member of a new class of falcipain-2 inhibitors and, unlike other peptide-based inhibitors, does not contain reactive groups that irreversibly bind to active cysteine sites.

  开发了一种384孔微量滴定板荧光切割测定法，用于鉴定半胱氨酸蛋白酶falcipain-2的抑制剂，falcipain-2是一个重要的抗疟药物靶点。通过生物活性导向分离自新加坡采集的土壤中分离得到的粘细菌Chitinophaga sp. Y23的甲醇提取物，鉴定出一种新的酰基四肽falcitidin（1），其对falcipain-2的IC50值为6μM。通过NMR和MS/MS分析确定了1的平面结构。由于产量低且不稳定（<100μg/L），尝试分离更多用于生物测试的样品受到阻碍。通过Marfey分析确定了1的绝对构型，并通过全合成确认其结构为异戊酸-D-组氨酸-L-异亮氨酸-L-缬氨酸-L-脯氨酸-NH2。Falcitidin（1）是新型falcipain-2抑制剂的首个成员，与其他基于肽的抑制剂不同，它不含有与活性半胱氨酸位点不可逆结合的反应性基团。
• Studies of Bitter Peptides from Casein Hydrolyzate. I. Synthesis of Bitter Peptide BPIa Corresponding to Arg–Gly–Pro–Pro–Phe–Ile–Val from Casein Hydrolyzate by Alkaline Proteinase of<i>Bacillus subtilis</i>
  作者：Hiroshi Fukui、Hidenori Kanehisa、Norio Ishibashi、Ichizo Miyake、Hideo Okai

  DOI：10.1246/bcsj.56.766

  日期：1983.3

  A bitter heptapeptide BPIa was synthesized and compared with the natural peptide, isolated by Minamiura et al. from casein hydrolyzate, by means of thin layer chromatography, paper electrophoresis, and carboxymethylcellulose column chromatography. All results for the two peptides matched very closely each other. The synthetic BPIa has an extremely bitter taste with its threshold value 0.05 mM. It is one of the most bitter compounds such as phenylthiourea and quinine.

  通过薄层色谱法、纸电泳法和羧甲基纤维素柱色谱法，合成了一种苦味七肽 BPIa，并将其与 Minamiura 等人从酪蛋白水解物中分离出的天然肽进行了比较。两种肽的所有结果都非常吻合。合成的 BPIa 具有极苦的味道，阈值为 0.05 mM。它是苯硫脲和奎宁等最苦的化合物之一。
• Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics
  作者：Gundala Chennakrishnareddy、Govindappa Nagendra、Hosahalli P. Hemantha、Ushati Das、Tayur N. Guru Row、Vommina V. Sureshbabu

  DOI：10.1016/j.tet.2010.06.082

  日期：2010.8

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.