benzyl N6-(tert-butoxycarbonyl)-D-lysinate | 240816-45-9

• 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: benzyl N6-(tert-butoxycarbonyl)-D-lysinate
• 英文别名: N⁶-Boc-D-lysine benzyl ester；N6-[(1,1-Dimethylethoxy)carbonyl]-D-lysine phenylmethyl ester；benzyl (2R)-2-amino-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 240816-45-9
• 化学式: C₁₈H₂₈N₂O₄
• 分子量: 336.431
• InChiKey: VFBUSCJNDZDRIB-OAHLLOKOSA-N

物化性质

• 沸点：
  465.4±40.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N6-(tert-butoxycarbonyl)-D-lysinate 在 sodium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 8.5h， 生成 (R)-benzyl 6-((R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(benzyloxy)-5-oxopentanamido)-2-(((benzyloxy)carbonyl)amino)hexanoate
  参考文献：
  名称：

  Structure−Activity Relationships in Nucleotide Oligomerization Domain 1 (Nod1) Agonistic γ-Glutamyldiaminopimelic Acid Derivatives

  摘要：

  N-Acyl-gamma-glutamyldiaminopimelic acid is a prototype ligand for Nod1. We report a detailed SAR of C-12-gamma-D-Glu-DAP. Analogues with glutaric or gamma-aminobutyric acid replacing the glutamic acid show greatly attenuated Nod1-agonistic activity. Substitution of the meso-diaminopimelic (DAP) acid component with monoaminopirnelic acid, L- or D-lysine, or cadaverine also results in reduced activity. The free amine on DAP is crucial. However, the N-acyl group on the D-glutamyl residue can be substituted with N-alkyl groups with full preservation of activity. The free carboxylates on the DAP and Glu components can also be esterified, resulting in more lipophilic but active analogues. Transcriptomal profiling showed a dominant up-regulation of IL-19, IL-20, IL-22, and IL-24, which may explain the pronounced Th2-polarizing activity of these compounds and also implicate cell signaling mediated by TREM-1. These results may explain the hitherto unknown mechanism of synergy between Nod1 and TLR agonists and are likely to be useful in designing vaccine adjuvants.

  DOI：

  10.1021/jm101535e
• 作为产物：
  描述：

  苯甲醇 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 二乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 benzyl N6-(tert-butoxycarbonyl)-D-lysinate
  参考文献：
  名称：

  Galactose cluster-pharmacokinetic modulator targeting moiety for siRNA

  摘要：

  本发明涉及用于靶向递送RNA干扰（RNAi）多核苷酸至体内细胞的组合物。药代动力学调节剂相较于单独的靶向配体能够提高体内靶向效果。靶向配体-药代动力学调节剂靶向基团靶向的RNAi多核苷酸可以单独或与共靶向递送聚合物一起在体内给予。

  公开号：

  US09249179B2

文献信息

• Synthesis of Four Lysine-Linked Cereulide Analogues Showing Ionophoric Activity Towards Potassium Cations as Lead Compounds for Emetic Toxin-Detection by Immunoassays
  作者：Minoru Isobe、Arthit Makarasen、Toshio Nishikawa

  DOI：10.1055/s-0029-1216837

  日期：2009.7

  An improved total synthesis of the emetic toxin cereulide and the preparation of four lysine-linked cereulide analogues is described. The cereulide analogues are prepared by replacing one of the amino acid residues in cereulide with lysine. The cereulide analogues demonstrate ionophoric activity towards alkali metal ions and inorganic ammonium ions, and are currently being used to develop an enzyme-linked immunosorbent assay for cereulide.

  描述了一种改进的呕吐毒素cereulide的总体合成及四种赖氨酸连接的cereulide类似物的制备。cereulide类似物是通过用赖氨酸替换cereulide中的一种氨基酸残基制备的。这些cereulide类似物对碱金属离子和无机铵离子表现出离子载体活性，目前正在用于开发针对cereulide的酶联免疫吸附测定法。
• [EN] FACTOR XIIa INHIBITORS<br/>[FR] INHIBITEURS DE FACTEUR XIIA
  申请人：MERCK SHARP & DOHME

  公开号：WO2018093716A1

  公开（公告）日：2018-05-24

  The present invention provides a compound of Formula I and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes. The compounds are selective Factor XIIa inhibitors.

  本发明提供了一种化合物I的化合物和包含一种或多种所述化合物的药物组合物，以及使用所述化合物用于治疗或预防血栓形成、栓塞、高凝血性或纤维化变化的方法。这些化合物是选择性的凝血因子XIIa抑制剂。
• Factor XIIa inhibitors
  申请人：Merck Sharp & Dohme Corp.

  公开号：US11014920B2

  公开（公告）日：2021-05-25

  The present invention provides a compound of Formula I and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes. The compounds are selective Factor XIIa inhibitors.

  本发明提供了一种式 I 的化合物和包含一种或多种所述化合物的药物组合物，以及使用所述化合物治疗或预防血栓形成、栓塞、高凝状态或纤维化变化的方法。所述化合物是选择性因子 XIIa 抑制剂。
• 一种JAK激酶抑制剂的前药
  申请人：[en]E-NITIATE BIOPHARMACEUTICALS (HANGZHOU) CO., LTD;[zh]启元生物（杭州）有限公司

  公开号：WO2024041586A1

  公开（公告）日：2024-02-29

  本发明涉及含JAK抑制剂的前药、组合物及其应用。特别地，本发明涉及式 (II) 所示的化合物、含有本发明化合物的药物组合物，及其作为JAK抑制剂前药在治疗炎症性疾病和肿瘤相关疾病中的用途。
• Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases
  作者：François Debaene、Julien A. Da Silva、Zbigniew Pianowski、Fernando J. Duran、Nicolas Winssinger

  DOI：10.1016/j.tet.2007.03.033

  日期：2007.7

  Seven PNA-encoded combinatorial libraries targeting proteases and phosphatases with covalent reversible and irreversible mechanism-based inhibitors were prepared. The libraries were synthesized using modified PNA monomers, which dramatically increase the water solubility of the libraries in biologically relevant buffers. The libraries were shown to selectively inhibit targeted enzymes. (c) 2007 Elsevier Ltd. All rights reserved.