BOC-L-鸟氨酸甲酯 | 78397-39-4

• 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: BOC-L-鸟氨酸甲酯
• 英文名称: Boc-Orn-OMe
• 英文别名: (S)-Methyl 5-amino-2-((tert-butoxycarbonyl)amino)pentanoate；methyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 78397-39-4
• 化学式: C₁₁H₂₂N₂O₄
• 分子量: 246.307
• InChiKey: DOKURIHNVIXJHI-QMMMGPOBSA-N

物化性质

• 沸点：
  360.5±37.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  BOC-L-鸟氨酸甲酯 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 Boc-L-鸟氨酸
  参考文献：
  名称：

  Inhibitors of N α-acetyl-l-ornithine deacetylase: synthesis, characterization and analysis of their inhibitory potency

  摘要：

  A series of N (alpha)-acyl (alkyl)- and N (alpha)-alkoxycarbonyl-derivatives of l- and d-ornithine were prepared, characterized, and analyzed for their potency toward the bacterial enzyme N (alpha)-acetyl-l-ornithine deacetylase (ArgE). ArgE catalyzes the conversion of N (alpha)-acetyl-l-ornithine to l-ornithine in the fifth step of the biosynthetic pathway for arginine, a necessary step for bacterial growth. Most of the compounds tested provided IC50 values in the mu M range toward ArgE, indicating that they are moderately strong inhibitors. N (alpha)-chloroacetyl-l-ornithine (1g) was the best inhibitor tested toward ArgE providing an IC50 value of 85 mu M while N (alpha)-trifluoroacetyl-l-ornithine (1f), N (alpha)-ethoxycarbonyl-l-ornithine (2b), and N (alpha)-acetyl-d-ornithine (1a) weakly inhibited ArgE activity providing IC50 values between 200 and 410 mu M. Weak inhibitory potency toward Bacillus subtilis-168 for N (alpha)-acetyl-d-ornithine (1a) and N (alpha)-fluoro- (1f), N (alpha)-chloro- (1g), N (alpha)-dichloro- (1h), and N (alpha)-trichloroacetyl-ornithine (1i) was also observed. These data correlate well with the IC50 values determined for ArgE, suggesting that these compounds might be capable of getting across the cell membrane and that ArgE is likely the bacterial enzymatic target.

  DOI：

  10.1007/s00726-009-0326-8
• 作为产物：
  描述：

  叔-丁基氯甲酸酯 在 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 生成 BOC-L-鸟氨酸甲酯
  参考文献：
  名称：

  Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors

  摘要：

  Recently, many natural products, especially some plant-derived polyphenols have been found to exert antiviral effects against influenza virus and show inhibitory activities on neuraminidases (NAs). In our research, we took caffeic acid which contained two phenolic hydroxyl groups as the basic fragment to build a small compound library with various structures. The enzyme inhibition result indicated that some compounds exhibited moderate activities against NA and compound 15d was the best with IC50 = 7.2 mu M and 8.5 mu M against N2 and N1 NAs, respectively. The 3,4-dihydroxyphenyl group from caffeic acid was important for the activity according to the docking analysis. Besides, compound 15d was found to be a non-competitive inhibitor with K-i = 11.5 +/- 0.25 mu M by the kinetic study and also presented anti-influenza virus activity in chicken embryo fibroblast cells. It seemed promising to discover more potent NA inhibitors from caffeic acid derivatives to cope with influenza virus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.033

文献信息

• Optimizing Protonation States for Selective Double-Strand DNA Photocleavage in Hypoxic Tumors: pH-Gated Transitions of Lysine Dipeptides
  作者：Kemal Kaya、Saumya Roy、Juan Carlos Nogues、Juan Camilo Rojas、Zlatko Sokolikj、Diego A. R. Zorio、Igor V. Alabugin

  DOI：10.1021/acs.jmedchem.6b01164

  日期：2016.9.22

  light-activated double-strand (ds) DNA cleavage is controlled by variations in electronic and geometric parameters. The conjugates have higher activities at the slightly acidic pH values that separate normal and cancerous tissue (pH < 7). This favorable pH dependence originates from several elements of structural design. Basicities of the two amines determine the threshold pH range where the changes in binding

  我们报告了新的二肽-乙炔共轭物家族的pH转换特性，其中pH门控的光活化双链（ds）DNA裂解受电子和几何参数变化的控制。结合物在弱酸性的pH值下具有较高的活性，该pH值将正常组织和癌变组织分开（pH <7）。这种有利的pH依赖性源于结构设计的几个要素。两种胺的碱性决定了观察到结合和反应性变化的阈值pH范围，而两个氨基和疏水性芳基炔烃部分之间的距离可以进一步调节DNA结合。质子化状态从中性分子到指示剂的变化导致ds DNA光裂解的效率大大提高，
• The Formation of Pyrroline and Tetrahydropyridine Rings in Amino Acids Catalyzed by Pyrrolysine Synthase (PylD)
  作者：Felix Quitterer、Philipp Beck、Adelbert Bacher、Michael Groll

  DOI：10.1002/anie.201402595

  日期：2014.7.28

  The dehydrogenase PylD catalyzes the ultimate step of the pyrrolysine pathway by converting the isopeptide L‐lysine‐Nε‐3R‐methyl‐D‐ornithine to the 22nd proteinogenic amino acid. In this study, we demonstrate how PylD can be harnessed to oxidize various isopeptides to novel amino acids by combining chemical synthesis with enzyme kinetics and X‐ray crystallography. The data enable a detailed description

  脱氢酶PylD通过将异肽L-赖氨酸-Nε -3 R-甲基-D-鸟氨酸转化为22个蛋白氨基酸来催化吡咯赖氨酸途径的最终步骤。在这项研究中，我们证明了如何结合化学合成，酶动力学和X射线晶体学方法，利用PylD将各种异肽氧化为新氨基酸。该数据使得能够详细描述作为吡咯赖氨酸类似物的成分的吡咯啉和四氢吡啶环的生物合成的PylD反应轨迹。
• CXCR4-ANTAGONISTIC DRUGS COMPRISING NITROGEN-CONTAINING COMPOUND
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：EP1389460A1

  公开（公告）日：2004-02-18

  To provide novel nitrogen-containing compounds having antagonism to CXCR4 and remedies for disease, such as rheumatism, cancer metastasis, etc., based on the CXCR4 antagonism. Nitrogen-containing compounds represented by the following general formula and CXCR4 antagonists containing these compounds as an active ingredient can be provided. The above compounds are typified by nitrogen-containing compounds represented by the following general formula (I) wherein A1 and A2 represent each a guanidino group or a group represented by the following general formula (ia) (wherein A3 represents a monocyclic or polycyclic heterocyclic aromatic ring group having 1 or 2 hetero atoms; B1 represents a single bond or alkylene group; and R1 represents hydrogen or alkyl group; W represents alkylene group having 2 to 3 carbon atoms, cyclic alkylene group having 5 to 10 carbon atoms, aromatic ring having 6 to 10 carbon atoms or heterocyclic aromatic ring having 5 to 10 carbon atoms; y is - (C=O) -; x is -C (=O) -NH-; n1 is an integer of 1 or 2; n2 is an integer of 2 or 3; and D is selected from among various substituents:

  为基于CXCR4拮抗作用提供对CXCR4具有拮抗作用的新型含氮化合物和治疗风湿病、癌症转移等疾病的药物。以下是一般式代表的含氮化合物和以这些化合物为活性成分的CXCR4拮抗剂。上述化合物以以下一般式（I）代表的含氮化合物为代表，其中A1和A2分别代表鸟氨基基团或由以下一般式（ia）代表的基团（其中A3代表具有1个或2个杂原子的单环或多环杂环芳香环基团；B1代表单键或烷基基团；R1代表氢或烷基基团；W代表具有2至3个碳原子的烷基基团、具有5至10个碳原子的环烷基团、具有6至10个碳原子的芳香环或具有5至10个碳原子的杂环芳香环；y为-(C=O)-；x为-C(=O)-NH-；n1为1或2的整数；n2为2或3的整数；D从各种取代基中选择）。
• Dopamine receptor modulation by conformationally constrained analogs of Pro-Leu-Gly-NH2
  作者：Kuo Long Yu、G. Rajakumar、Lalit K. Srivastava、Ram K. Mishra、Rodney L. Johnson

  DOI：10.1021/jm00402a031

  日期：1988.7

  Leu-Gly-NH2 dipeptide segment of PLG was replaced with the gamma-lactam residues 3(S)- and 3(R)-amino-2-oxopyrrolidineacetamide and the delta-lactam residue 3(S)-amino-2-oxopiperidineacetamide. The corresponding gamma-lactam analogues of less than Glu-Leu-Gly-NH2 were also synthesized. In a second series of analogues, the glycinamide residue of PLG was replaced with the 2-ketopiperazine, 3(S)-amino-2-pyrrolidone

  已合成了两个系列的Pro-Leu-Gly-NH2（PLG）构象受限的类似物。在一系列类似物中，PLG的Leu-Gly-NH2二肽片段被γ-内酰胺残基3（S）-和3（R）-氨基-2-氧吡咯烷乙酰胺和δ-内酰胺残基3（S）取代-氨基-2-氧代哌啶乙酰胺。还合成了小于Glu-Leu-Gly-NH 2的相应的γ-内酰胺类似物。在第二系列类似物中，PLG的甘氨酰胺残基被2-酮戊哌嗪，3（S）-氨基-2-吡咯烷酮和3（S）-氨基-2-哌啶酮残基取代。测试上述类似物增强多巴胺受体激动剂2-氨基-6,7-二羟基-1,2,3,4-四氢萘（ADTN）与纹状体多巴胺受体结合的能力。在这项研究中合成的受PLG构象约束的类似物中，只有γ-内酰胺类似物3（R）-（NL-脯氨酰胺基）-2-氧代-1-吡咯烷乙酰胺（3）被发现具有显着活性。在预温育条件下，该类似物的活性是PLG的10,000倍。它在10（-9）和10（-10）M浓度下显着增强了ADTN的结合。
• Discovery of Cofactor Competitive Inhibitors against the Human Methyltransferase Fibrillarin
  作者：Yun Shi、Ibrahim M. El-Deeb、Veronika Masic、Lauren Hartley-Tassell、Andrea Maggioni、Mark von Itzstein、Thomas Ve

  DOI：10.3390/ph15010026

  日期：——

  spectroscopy, yielded seven hit compounds that competed with cofactor binding, two of which resulted in co-crystal structures. One of these structures revealed unexpected conformational variability in the cofactor binding site, which allows it to accommodate a compound significantly different from SAM. Our structural data provide critical information for the design of selective cofactor competitive inhibitors

  原纤维蛋白 (FBL) 是一种必需且进化上高度保守的 S-腺苷甲硫氨酸 (SAM) 依赖性甲基转移酶。它是多蛋白复合物的催化成分，可促进核糖体 RNA (rRNA) 的 2′- O-甲基化，这是真核细胞中准确有效的蛋白质合成所必需的修饰。最近确定，人类 FBL (hFBL) 对于尼帕病毒、亨德拉病毒和呼吸道合胞病毒感染至关重要。此外，hFBL 的过度表达有助于肿瘤发生，并与乳腺癌患者的生存不良相关，这表明 hFBL 是开发抗病毒和抗癌药物的潜在靶点。针对辅因子依赖性酶的一个有吸引力的策略是选择性抑制辅因子结合，该策略已成功开发针对几种蛋白质甲基转移酶（包括 PRMT5、DOT1L 和 EZH2）的抑制剂。在这项工作中，我们解析了 apo 形式的 hFBL 甲基转移酶结构域及其与辅因子 SAM 复合物的晶体结构。通过 X 射线晶体学和 19F NMR 光谱筛选氟化片段库，产生了七种与辅因子结