Boc-Leu-Ser-OMe | 40290-54-8

• 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: Boc-Leu-Ser-OMe
• 英文别名: methyl (2S)-3-hydroxy-2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]propanoate
• CAS: 40290-54-8
• 化学式: C₁₅H₂₈N₂O₆
• 分子量: 332.397
• InChiKey: HQWMBMNQIQPYJT-QWRGUYRKSA-N

物化性质

• 沸点：
  519.8±45.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Leu-Ser-OMe 在 N-甲基吗啉 、 盐酸 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 、 仲丁醇 为溶剂， 反应 3.5h， 生成 (2S,5S)-2-hydroxymethyl-5-iso-butyl-3,6-diketopiperazine
  参考文献：
  名称：

  Cyclic dipeptides exhibit potency for scavenging radicals

  摘要：

  Twenty kinds of cyclic dipeptides containing L-leucine were synthesized, and their antioxidant activity against (OH)-O-center dot and O-2(center dot-) was investigated. Compounds possessing polar amino acid residues, such as Asp, Cys, Glu, Lys, Pro, Ser, and Trp, exhibited higher antioxidant activity against (OH)-O-center dot than vitamin E. However, only cyclo(L-Cys-L-Leu) scavenged O-2(center dot-). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.050
• 作为产物：
  描述：

  methyl O-benzyl-N-((tert-butoxycarbonyl)-L-leucyl)-L-serinate 在 氢气 、 钯 作用下， 以 乙醇 为溶剂， 以89%的产率得到Boc-Leu-Ser-OMe
  参考文献：
  名称：

  sansalvamide A 肽模拟物的合成：含有三唑、恶唑、噻唑和假脯氨酸的化合物

  摘要：

  与用肽类似物观察到的相比，基于肽模拟物的大环化合物通常具有改进的药代动力学特性。描述了基于活性 sansalvamide A 结构的 13 种拟肽衍生物的合成，其中这些类似物沿大环骨架包含杂环（三唑、恶唑、噻唑或假脯氨酸）。这些衍生物的合成采用了几种可用于将大环肽转化为其拟肽对应物的方法。这些方法包括肽修饰以生成用于点击化学的炔烃和叠氮化物、丝氨酸转化为恶唑、Hantzsch 反应生成噻唑以及保护苏氨酸生成假脯氨酸衍生物。此外，我们展示了两种不同的拟肽部分，三唑和噻唑，

  DOI：

  10.1016/j.tet.2011.11.089

文献信息

• Catalytic activation of glycosyl phosphates for stereoselective coupling reactions
  作者：Samuel M. Levi、Qiuhan Li、Andreas R. Rötheli、Eric N. Jacobsen

  DOI：10.1073/pnas.1811186116

  日期：2019.1.2

  Glycosyl phosphates are shown to be activated to stereospecific nucleophilic substitution reactions by precisely tailored bis-thiourea catalysts. Enhanced reactivity and scope is observed with phosphate relative to chloride leaving groups. Stronger binding (Km) to the H-bond donor and enhanced reactivity of the complex (kcat) enables efficient catalysis with broad functional group compatibility under

  糖基磷酸酯已显示通过精确定制的双硫脲催化剂被激活成立体定向亲核取代反应。相对于氯化物离去基团，磷酸盐具有增强的反应性和范围。与氢键供体的更强结合（K m）和配合物（k cat）的增强的反应性可在温和，中性条件下以广泛的官能团相容性实现高效催化。
• Synthesis, Characterization and Biological Evaluation of Cyclic Peptides: Viscumamide, Yunnanin A and Evolidine
  作者：Boja Poojary、S. L. Belagali

  DOI：10.1515/znb-2005-1217

  日期：2005.12.1

  Three biologically active cyclic peptides, viscumamide, yunnanin A and evolidine were synthesized and the structures were established on the basis of analytical, IR, NMR and mass spectral data. These newly synthesized cyclic peptides were evaluated for antimicrobial and pharmacological activities. Evolidine showed better growth inhibition against bacterial strains than yunnanin A and viscumamide. The anti-inflammatory activity of viscumamide is moderate and the remaining two cyclic peptides are found to be less active. But, all the three cyclic peptides showed weak anthelmintic activity.

  三种生物活性环肽，viscumamide、yunnanin A和evolidine被合成，并根据分析、红外线、核磁共振和质谱数据确定了它们的结构。这些新合成的环肽被评估其抗微生物和药理活性。Evolidine对细菌菌株的生长抑制作用优于yunnanin A和viscumamide。Viscumamide的抗炎活性中等，而另外两种环肽的活性较低。但是，这三种环肽都显示出弱的驱虫活性。
• Parallel synthesis of bis-oxazole peptidomimetics
  作者：Siva Murru、Colette T. Dooley、Adel Nefzi

  DOI：10.1016/j.tetlet.2013.10.078

  日期：2013.12

  The parallel synthesis of bis-oxazole peptidomimetics starting from Boc-aminoacids and Serine-methyl ester is described. This work presents the synthesis of oxazole aminoacid building blocks in solution phase and their utilization for the solid phase peptide synthesis of a library of diverse bis-oxazole peptidomimetics in good overall yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Combinatorial Synthesis of Oxazol-Thiazole Bis-Heterocyclic Compounds
  作者：Siva Murru、Adel Nefzi

  DOI：10.1021/co400133a

  日期：2014.1.13

  A combinatorial library of novel oxazol-thiazole bis-heterocycles was synthesized in good to excellent overall yields with high purity using a solution and solid-phase parallel synthesis approach. Oxazole amino acids, prepared from serine methyl ester and amino acids via coupling and cyclodehydration, were treated with Fmoc-NCS and alpha-haloketones for the parallel synthesis of diverse bis-heterocycles. Fmoc-isothiocyanate is used as a traceless reagent for thiazole formation. Oxazole diversity can be achieved by using variety of amino acids, whereas thiazole diversity is produced with various haloketones.
• Syntheses of [12]aneN3–oligopeptide conjugates as effective DNA condensation agents
  作者：Zhi-Fen Li、Zhi-Fo Guo、Hao Yan、Zhong-Lin Lu、Da-Yong Wu

  DOI：10.1016/j.bmc.2012.03.022

  日期：2012.5

  With the aim to develop effective and low toxicity DNA condensation agents, a series of oligopeptide derived macrocyclic polyamine [12]aneN(3) conjugates 7a-h center dot 3HCl have been designed and synthesized through multi-step amidation reactions. Structure-property study through gel electrophoresis proved that the conjugates containing high hydrophobic ending amino acids exhibited effective condensation ability at concentration of 150-250 mu M, which was further confirmed by dynamic light scattering and atomic force microscopy experiments. EB displacement assay, ionic salt effect, and structure-property relationship in gel electrophoresis indicated that DNA condensation resulted from both the electrostatic interaction of [12]aneN(3) unit and hydrogen-bonding/hydrophobic multi-interaction of oligopeptide moiety in the conjugates with DNA. The reversible condensation process and their low cytotoxicity suggest that the new condensing agents are potential for the development of non-viral vectors. (C) 2012 Elsevier Ltd. All rights reserved.