Boc-Leu-O-COO-isoBu | 66866-44-2

• 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-Leu-O-COO-isoBu
• 英文别名: 2-methylpropoxycarbonyl (2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 66866-44-2
• 化学式: C₁₆H₂₉NO₆
• 分子量: 331.409
• InChiKey: BWBOEYPNOPHGFT-LBPRGKRZSA-N

物化性质

• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Leu-O-COO-isoBu 在 N-甲基吗啉 、 盐酸 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 水 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.45h， 生成 4-((S)-3-((S)-1-(6-(benzylcarbamoyl)-4'-carbamoylbiphenyl-3-ylamino)-4-methyl-1-oxopentan-2-ylamino)-2-(4-cyanobenzamido)-3-oxopropyl)phenyl dihydrogen phosphate
  参考文献：
  名称：

  Design, synthesis, and in vitro characterization of novel hybrid peptidomimetic inhibitors of STAT3 protein

  摘要：

  Aberrant activation of oncogenic signal transducer and activator of transcription 3 (STAT3) protein signaling pathways has been extensively implicated in human cancers. Given STAT3's prominent dysregulatory role in malignant transformation and tumorigenesis, there has been a significant effort to discover STAT3-specific inhibitors as chemical probes for defining the aberrant STAT3-mediated molecular events that support the malignant phenotype. To identify novel, STAT3-selective inhibitors suitable for interrogating STAT3 signaling in tumor cells, we explored the design of hybrid molecules by conjugating a known STAT3 inhibitory peptidomimetic, ISS610 to the high-affinity STAT3-binding peptide motif derived from the ILR/gp-130. Several hybrid molecules were examined in in vitro biophysical and biochemical studies for inhibitory potency against STAT3. Lead inhibitor 14aa was shown to strongly bind to STAT3 (K-D = 900 nM), disrupt STAT3: phosphopeptide complexes (K-i = 5 mu M) and suppress STAT3 activity in in vitro DNA binding activity/electrophoretic mobility shift assay (EMSA). Moreover, lead STAT3 inhibitor 14aa induced a time-dependent inhibition of constitutive STAT3 activation in v-Src transformed mouse fibroblasts (NIH3T3/v-Src), with 80% suppression of constitutively-active STAT3 at 6 h following treatment of NIH3T3/v-Src. However, STAT3 activity recovered at 24 h after treatment of cells, suggesting potential degradation of the compound. Results further showed a suppression of aberrant STAT3 activity in NIH3T3/v-Src by the treatment with compound 14aa-OH, which is the non-pTyr version of compound 14aa. The effect of compounds 14aa and 14aa-OH are accompanied by a moderate loss of cell viability. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.010
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 N-甲基吗啉 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.75h， 生成 Boc-Leu-O-COO-isoBu
  参考文献：
  名称：

  利用自然界的结构多样性：开发用于钌催化的酮的对映选择性转移氢化的模块化二肽类似物配体。

  摘要：

  基于叔丁氧羰基（N-Boc）-保护的α-氨基酸和手性邻位氨基醇的组合，制备了新颖的二肽-类似物配体的文库。这些高度模块化的配体与[[RuCl（2）（p-cymene）]（2）]结合，并筛选得到的金属配合物作为催化剂，用于在转移氢化条件下使用2-丙醇作为氢供体的对苯乙酮对映选择性还原。用几种新颖的催化剂可获得极好的1-苯基乙醇对映体选择性（ee高达98％）。尽管大多数配体包含两个立体中心，但已证明产物醇的绝对构型是由配体的氨基酸部分的构型决定的。利用基于L-氨基酸的配体生成S-构型产物，基于D-氨基酸的催化剂有利于R-构型醇的形成。N-Boc-L-丙氨酸和（R）-苯基甘醇（Boc-L-Ab）或其对映异构体（N-Boc-D-丙氨酸和（S）-苯基甘醇，Boc-D-Aa）的组合被证明是还原过程的最佳配体。评估了许多芳基烷基酮的转移氢化反应，并获得了极佳的对映选择性，最高可达96％ee。

  DOI：

  10.1002/chem.200304900

文献信息

• <i>α-N</i>-Protected dipeptide acids: a simple and efficient synthesis via the easily accessible mixed anhydride method using free amino acids in DMSO and tetrabutylammonium hydroxide
  作者：G. Verardo、A. Gorassini

  DOI：10.1002/psc.2503

  日期：2013.5

  to find simple and efficient methods for their synthesis. For this reason, we have investigated the synthesis of α‐N‐protected dipeptide acids by reacting the easily accessible mixed anhydride of α‐N‐protected amino acids with free amino acids under different reaction conditions. The combination of TBA‐OH and DMSO has been found to be the best to overcome the low solubility of amino acids in organic

  在医学和药理学领域中，二肽的重要性已得到充分证明，并且已进行了许多努力来寻找简单有效的合成方法。因此，我们通过使易于获得的α-N混合酸酐反应，研究了α-N保护的二肽酸的合成在不同的反应条件下用游离氨基酸保护氨基酸。已经发现，TBA-OH和DMSO的组合是克服氨基酸在有机溶剂中低溶解度的最佳方法。在这些实验条件下，均相缩合反应迅速发生且没有可检测的差向异构。本方法也适用于未保护的侧链Tyr，Trp，Glu和Asp，但不适用于Lys。后一个残基能够结合两个混合酸酐分子，得到相应的异三肽。此外，已经测试了该方案对三肽和四肽合成的适用性。这种方法减少了对保护基的需求，具有成本效益，可扩展性，并产生了可用作较大肽合成的基础材料的二肽酸。
• Coupling Reagent Dependent Regioselectivity in the Synthesis of Lysine Dipeptides
  作者：Shimon Shatzmiller、Pat N. Confalone、Ariela Abiri

  DOI：10.1055/s-1999-3178

  日期：——

  Participation of either the Nℇ or Nα of l-methyl lysinate (2) in peptide bond formation could be selectively achieved by the use of either isobutyl chloroformate (method A) or N,N-bis(2-oxo-3-oxazolidinyl) phosphinic chloride (BOP-Cl) (method B), respectively. The amidation performed according to method A gives high yields of the dipeptides 3a-e, irrespective of the amino acids used. In method B, Nα amidation is highly preferred especially with bulky amino acids, yielding 4a, 4c and 4e. The less bulky 4b and 4d gave 4.5 and 20 regioselection Nα/Nℇ amidation ratios. A mechanistical rationalization for these selectivities is discussed.

  可以使用异丁基氯甲酸酯（方法A）或N,N-双（2-氧代-3-噁唑啉基）磷酰氯（BOP-Cl）（方法B）分别选择性地实现赖氨酸（2）的Nα或Nε参与的肽键形成。按照方法A进行的酰胺化反应能够高产率地得到二肽3a-e，不受所用氨基酸的影响。在方法B中，Nα酰胺化反应特别倾向于与体积较大的氨基酸反应，生成4a、4c和4e。体积较小的4b和4d则分别得到4.5和20的Nα/Nε酰胺化选择比。本文讨论了这些选择性的机制解释。
• Highly Enantioselective Ruthenium-Catalyzed Reduction of Ketones Employing Readily Available Peptide Ligands
  作者：Anders Bøgevig、Isidro M. Pastor、Hans Adolfsson

  DOI：10.1002/chem.200305553

  日期：2004.1.5

  Highly efficient and selective catalysts for the asymmetric reduction of aryl alkyl ketones under hydrogen-transfer conditions (2-propanol) were obtained by combining a novel class of pseudo-dipeptide ligands with [[RuCl(2)(p-cymene)](2)]. A library of 36 dipeptide-like ligands was prepared from N-Boc-protected alpha-amino acids and the enantiomers of 2-amino-1-phenylethanol and 1-amino-2-propanol

  通过将新型伪二肽配体与[[RuCl（2）（p-cymene）]（2 ）]。由N-Boc保护的α-氨基酸和2-氨基-1-苯基乙醇和1-氨基-2-丙醇的对映异构体制备了36种二肽样配体的文库。用苯乙酮的还原来评估催化剂库，并且用几种新型催化剂获得了1-苯基乙醇的优异对映选择性。发现基于N-Boc-L-丙氨酸和（S）-1-氨基-2-丙醇（配体A-（S）-4）的组合的配体特别有效。当该配体的原位形成的钌络合物用作各种芳基烷基酮的氢转移反应的催化剂时，
• Asymmetric transfer hydrogenation of ketones catalyzed by rhodium complexes containing amino acid triazole ligands
  作者：Fredrik Tinnis、Hans Adolfsson

  DOI：10.1039/c0ob00400f

  日期：——

  Active and selective catalysts for the asymmetric reduction of ketones, under transfer hydrogenation conditions, were obtained by combining [RhCl2Cp*]2, with a series of L-amino acid thioamide ligands functionalized with 1,2,3-triazoles. The obtained secondary alcohol products were formed with up to 93% ee.

  通过转移加氢条件获得了用于酮不对称还原的活性和选择性催化剂。 [RhCl 2 Cp *] 2，带有一系列 L-氨基酸硫代酰胺1,2,3-三唑官能化的配体。所形成的仲醇产物具有高达93％的ee。
• Direct asymmetric N-specific reaction of nitrosobenzene with aldehydes catalyzed by a chiral primary amine-based organocatalyst
  作者：Long Qin、Lei Li、Lei Yi、Chao-Shan Da、Yi-Feng Zhou

  DOI：10.1002/chir.20960

  日期：2011.8

  interesting and important to perform a nitrogen or oxygen selective reaction with interesting substrates. These atom specific reactions are crucial to specifically synthesis of specific compounds. An enantioselective N‐specific reaction of nitrosobenzene with unmodified aldehydes was successfully achieved catalyzed first by a variety of primary amine‐based organocatalysts with higher yield and enantioselectivity

  亚硝基化合物具有两个反应性氮原子和氧原子。与感兴趣的底物进行氮或氧选择性反应是有趣且重要的。这些原子特异性反应对于特异性合成特定化合物至关重要。亚硝基苯与未修饰醛的对映选择性N特异性反应是首先通过多种具有较高收率和对映选择性的伯胺基有机催化剂成功催化的。有机催化剂中较大的取代基和有机催化剂中的两个氢键以及亚硝基苯的氧原子优先使反应成为N特异性的，并主要提供R产物。手性，2011年。©2011 Wiley‐Liss，Inc.。