Boc-Lys(Z)-Pro-OBzl | 68280-74-0

• 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-Lys(Z)-Pro-OBzl
• 英文别名: benzyl N⁶-((benzyloxy)carbonyl)-N²-(tert-butoxycarbonyl)-L-lysyl-L-prolinate；benzyl (2S)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoyl]pyrrolidine-2-carboxylate
• CAS: 68280-74-0
• 化学式: C₃₁H₄₁N₃O₇
• 分子量: 567.682
• InChiKey: RTHLXCRAOVUBKU-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  123.27
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Boc-Lys(Z)-Pro-OBzl 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以89.2%的产率得到Boc-Lys(Z)-Pro-OH
  参考文献：
  名称：

  2, 3-二氯苯基哌嗪二肽的尿素和硫脲衍生物对脲酶活性的抑制

  摘要：

  目的：酶抑制研究仍然是药物研究的一个重要领域，因为这些研究导致发现了用于各种生理条件的药物。为了寻找新型脲酶抑制剂，合成了四种二肽，与 2,3-二氯苯基哌嗪类似物缀合并转化为尿素/硫脲衍生物。方法：通过溶液相法合成肽，并使用 1-乙基-3-（3-二甲基氨基丙基）碳二亚胺（EDCI）/羟基苯并三唑（HOBt）作为偶联剂和 N -甲基吗啉（NMM）作为碱。使用三氟乙酸 (TFA) 去除叔丁氧羰基 (Boc) 基团，用 NMM 中和并分别使用取代的异氰酸苯酯和异硫氰酸酯转化为尿素和硫脲衍生物。结果：大多数合成的类似物被发现是脲酶酶活性的良好抑制剂。在间位或对位具有 F 和 Cl 取代基的硫脲的缀合物显示出主要的脲酶抑制活性。类似物 23 的效力比参考标准品 21.0±0.11 µM 强近 10 倍 (2 µM)。结论：报告的活性与一些文献报道的脲酶抑制剂相关，发现我们的化合物 23 比现有化合物更有效。在间位或对位具有

  DOI：

  10.22159/ijpps.2017v9i9.19425
• 作为产物：
  描述：

  N-Boc-N'-Cbz-L-赖氨酸 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 Boc-Lys(Z)-Pro-OBzl
  参考文献：
  名称：

  NAcSDKP Analogues Resistant to Angiotensin-Converting Enzyme

  摘要：

  Two series of analogues of the tetrapeptide NAcSDKP, an inhibitor of hematopoietic stem cell proliferation, were prepared, and their enzymatic stability toward rabbit lung angiotensin-converting enzyme (ACE) was evaluated as well as their capacity to inhibit NAcSDKP hydrolysis by this enzyme. In the first series, each of the peptide bonds has been successively replaced by an aminomethylene bond. In the second one, the C-terminus of the peptide has been modified by decarboxylation or amidation. The results reported here indicate that all of these molecules but one have good stability toward the enzyme but none of the compounds is able to inhibit NAcSDKP hydrolysis by ACE.

  DOI：

  10.1021/jm9701132

文献信息

• Solution-Phase Automated Synthesis of Tripeptide Derivatives.
  作者：Noritaka KURODA、Taeko HATTORI、Chieko KITADA、Tohru SUGAWARA

  DOI：10.1248/cpb.49.1138

  日期：——

  An improved general method for automated synthesis of tripeptides was developed, in which methanesulfonic acid (MSA) was used in place of trifluoroacetic acid (TFA), thus making it possible to avoid, 1) corrosion of the apparatus by strong acid vapor, 2) formation of emulsions, and 3) use of the restricted solvent, dichloromethane. As an application of the automated synthesis apparatus, 216 fragment tripeptide derivatives were synthesized systematically using the MSA method, in excellent yield and with increased efficiency.

  开发了一种改进的用于三肽自动化合成的一般方法，在该方法中使用甲磺酸（MSA）代替三氟乙酸（TFA），从而避免了以下问题：1）强酸蒸汽对设备的腐蚀，2）乳液的形成，以及3）使用受限的溶剂二氯甲烷。作为自动化合成设备的应用，使用MSA方法系统地合成了216种片段三肽衍生物，产量极高，效率提高。
• Synthesis and bioactivity of a Goralatide analog with antileukemic activity
  作者：Zhiliang Li、Iryna O. Lebedyeva、Vita M. Golubovskaya、William G. Cance、Khalid A. Alamry、Hassan M. Faidallah、C. Dennis Hall、Alan R. Katritzky

  DOI：10.1016/j.bmc.2015.04.061

  日期：2015.8

  stable in vivo and decomposes within 4.5 min when applied to live cells. In this work we developed an analog of Goralatide that exhibits cytotoxicity towards human myeloid HL-60, HEL, Nalm-6 leukemia cells, endothelial HUVEC, glioblastoma U251 and transformed kidney 293T cells. The Goralatide analog showed significant stability in organic solution with no tendency to degrade oxidatively.

  天然四肽Goralatide（AcSDKP）是原始造血细胞增殖的选择性抑制剂。它在体内不稳定，当应用于活细胞时会在4.5分钟内分解。在这项工作中，我们开发了一种Goralatide的类似物，该类似物对人骨髓HL-60，HEL，Nalm-6白血病细胞，内皮HUVEC，胶质母细胞瘤U251和转化的肾293T细胞具有细胞毒性。高拉来肽类似物在有机溶液中显示出显着的稳定性，没有氧化降解的趋势。
• Synthesis and activity of NAcSerAspLysPro analogs on cellular interactions between T-cell and erythrocytes in rosette formation
  作者：Josiane Thierry、Marie Pierre Papet、Nathalie Saez-Servent、Jacqueline Plissonneau-Haumont、Pierre Potier、Maryse Lenfant

  DOI：10.1021/jm00170a012

  日期：1990.8

  Analogues of NAcSerAspLysPro (AcSDKP), a natural regulator of hematopoiesis isolated from fetal calf bone marrow, were synthesized. The biological activity of these molecules were evaluated in vitro in the rosette assay, which measures the interaction between human Jurkat T-cells and sheep red blood cells. In this test, the tripeptide SerAspLys was the most efficient. Inhibitory activity was detected at the concentration 10(-14) M for the analogue and at 10(-9) M for the parent tetrapeptide. The dipeptide NAcSerAsp still showed activity but at much higher doses (10(-6) M). Substitution of polar amino acids led mostly to inactive molecules. Thus, replacement of Ser by Ala, or Lys by Orn yielded completely inactive compounds and replacement of Asp by Glu decreased the activity (10(-6) M). The present study gives an insight into the role of individual amino acids of AcSDKP in the inhibition of the rosette formation which implicates interactions with T-cell CD2 glycoprotein.
• BIENERT, M.;LINDNER, G.;GROSS. E, G.;JENTZSCH, K. -D.;OEHME, P.
  作者：BIENERT, M.、LINDNER, G.、GROSS. E, G.、JENTZSCH, K. -D.、OEHME, P.

  DOI：——

  日期：——