3-[2-Amino-3-(2-ethoxycarbonyl-ethoxy)-2-(2-ethoxycarbonyl-ethoxymethyl)-propoxy]-propionic acid ethyl ester | 132491-90-8

• 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: 3-[2-Amino-3-(2-ethoxycarbonyl-ethoxy)-2-(2-ethoxycarbonyl-ethoxymethyl)-propoxy]-propionic acid ethyl ester
• 英文别名: tris(carboxyethoxymethyl)aminomethane triethyl ester；ethyl 3-[2-amino-3-(3-ethoxy-3-oxopropoxy)-2-[(3-ethoxy-3-oxopropoxy)methyl]propoxy]propanoate
• CAS: 132491-90-8
• 化学式: C₁₉H₃₅NO₉
• 分子量: 421.488
• InChiKey: SDVGDBABZRZRBL-UHFFFAOYSA-N

物化性质

• 沸点：
  494.6±45.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  29
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-[2-Amino-3-(2-ethoxycarbonyl-ethoxy)-2-(2-ethoxycarbonyl-ethoxymethyl)-propoxy]-propionic acid ethyl ester 在 sodium carbonate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 benzyl N-tris[(2-carboxyethyloxy)methyl]methylcarbamate
  参考文献：
  名称：

  与三个顺序连接的N-乙酰半乳糖胺部分相连的肽核酸向肝细胞的受体特异性传递。

  摘要：

  肽核酸（PNA）是DNA类似物，它们以序列特异性方式与DNA和RNA高亲和力结合，但细胞通透性差，限制了其作为治疗剂的用途。此处描述的工作是受最近报道的，即通过与三触角N-乙酰半乳糖胺（GalNAc）（脱唾液酸糖蛋白受体（ASGPR）识别的配体）缀合的小干扰RNA在肝细胞中有效进行基因沉默所激发。的PNA缀合到在N末端或者三触角的GalNAc（支化结构），或位于C锚定的单体的GalNAc部分γ的三个连续的PNA单体的ñ - （2-氨基乙基）甘氨酸（AEG在固相上合成支架（顺序结构）。如紫外和圆二色光谱法所示，它们与互补的DNA和RNA形成双链体。GalNAc偶联的PNA的荧光标记类似物被表达ASGPR的HepG2细胞内在化，但缺少该受体的HEK-293细胞却不吸收。如共聚焦显微镜所证实的，相继缀合物比分支缀合物更有效地内化到HepG2细胞中，大约13倍。此处提出的结果突出了GalNAc偶联

  DOI：

  10.1021/acs.joc.0c00601
• 作为产物：
  描述：

  benzyl N-tris[(2-carboxyethyloxy)methyl]methylcarbamate 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 苯 为溶剂， 生成 3-[2-Amino-3-(2-ethoxycarbonyl-ethoxy)-2-(2-ethoxycarbonyl-ethoxymethyl)-propoxy]-propionic acid ethyl ester
  参考文献：
  名称：

  Self-Association of Protected Newkome-Type Second-Generation Dendrimers at Nanomolar Level Concentrations in Aqueous Solution

  摘要：

  Protected Newkome-type second-generation dendrimers (based on Lin's amine) were synthesized with a pyrene moiety attached to the core. The photophysical property in aqueous solution of the protected dendrimers shows self-association behavior in water. Pyrene excimer emission at 475 nm is observed in water even at very low concentrations of protected dendrimer (ca. 5 x 10(-8) M). This emission band is absent in other solvents even up to a concentration of 10(-5) M. The corresponding unprotected dendrimer does not show the pyrene excimer fluorescence. The amide of pyrene butyric acid with tert-butylamine shows the formation of excimer, albeit with very low intensity. Quenching studies on the dendrimer with hydrophilic quencher iodide anion (I-) reveal that there is significant quenching of fluorescence intensity in the case of N-tert-butyl-4-pyren-1-ylbutyramide as compared to that of the pyrene-attached second-generation protected dendrimer. This shows that the pyrene moiety in the case of the protected dendrimer is significantly shielded from the surrounding.

  DOI：

  10.1021/ma0498215

文献信息

• [EN] NUCLEIC ACID CONJUGATES AND USES THEREOF<br/>[FR] CONJUGUÉS DE TYPE ACIDE NUCLÉIQUE ET LEURS UTILISATIONS
  申请人：TRANSLATE BIO MA INC

  公开号：WO2018013525A1

  公开（公告）日：2018-01-18

  Provided herein are conjugates comprising targeting moieties such as sugars, folates and cell-penetrating peptides, which can be used for the improved delivery of agents (e.g., nucleic acids, such as oligonucleotides or mRNAs, or other agents) to cells. The invention provides conjugates and compounds comprising targeting moieties, methods for preparing the same, and intermediates useful in their preparation. In another aspect, the present invention provides formulations (e.g., pharmaceutical compositions) comprising the targetting moiety-containing conjugates and compounds. The present invention also provides methods for delivering agents (e.g., nucleic acids such as oligonucleotides or mRNAs) to a cell, methods for treating and/or preventing a disease or condition in a subject, and methods for modulating gene expression in a cell or a subject. Further, provided herein are kits comprising the conjugates, or formulations thereof; and kits for the preparation of conjugates described herein.

  本文提供了包含靶向基团的共轭物，如糖类、叶酸和穿膜肽，可用于改善药物（例如核酸，如寡核苷酸或mRNA，或其他药物）对细胞的传递。该发明提供了包含靶向基团的共轭物和化合物，以及其制备方法和制备过程中有用的中间体。另一方面，本发明提供了包含靶向基团的共轭物和化合物的配方（例如，药物组合物）。本发明还提供了将药物（例如核酸，如寡核苷酸或mRNA）传递至细胞的方法，用于治疗和/或预防受试者疾病或状况的方法，以及用于调节细胞或受试者基因表达的方法。此外，本文提供了包含这些共轭物或其配方的试剂盒；以及用于制备本文所述共轭物的试剂盒。
• Facile synthesis of size dependent Ru(ii)–carbohydrate dendrimers via click chemistry
  作者：Raghavendra Kikkeri、Xinyu Liu、Alexander Adibekian、Yu-Hsuan Tsai、Peter H. Seeberger

  DOI：10.1039/b925113h

  日期：——

  A facile and flexible approach for the preparation of Ru(II) complexes containing different carbohydrates based on the Cu(II)-catalyzed Huisgen-[3+2] cycloaddition is described.

  描述了一种基于Cu（II）催化的Huisgen- [3 + 2]环加成反应制备包含不同碳水化合物的Ru（II）配合物的简便灵活的方法。
• [EN] CONJUGATED ANTISENSE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS ANTISENS CONJUGUÉS ET LEUR UTILISATION
  申请人：ISIS PHARMACEUTICALS INC

  公开号：WO2014179620A1

  公开（公告）日：2014-11-06

  Provided herein are oligomeric compounds with conjugate groups. In certain embodiments, the oligomeric compounds are conjugated to N-Acetylgalactosamine.

  本文提供了具有共轭基团的寡聚化合物。在某些实施例中，这些寡聚化合物与N-乙酰半乳糖结合。
• [EN] TARGETED THERAPEUTIC NUCLEOSIDES AND THEIR USE<br/>[FR] NUCLÉOSIDES THÉRAPEUTIQUES CIBLÉES ET LEUR UTILISATION
  申请人：ISIS PHARMACEUTICALS INC

  公开号：WO2015042447A1

  公开（公告）日：2015-03-26

  Provided herein are compounds comprising one or more therapeutic nucleosides and one or more targeting groups. In certain embodiments, the compounds further comprise one or more oligonucleotides. In certain embodiments, a targeting group comprises one or more N-Acetylgalactosamine.

  本文提供的化合物包括一个或多个治疗性核苷和一个或多个靶向基团。在某些实施例中，这些化合物进一步包括一个或多个寡核苷酸。在某些实施例中，一个靶向基团包括一个或多个N-乙酰半乳糖胺。
• Synthesis and Excellent Duplex Stability of Oligonucleotides Containing 2′-Amino-LNA Functionalized with Galactose Units
  作者：Rajesh Kumar、Annika Ries、Jesper Wengel

  DOI：10.3390/molecules22050852

  日期：——

  A convenient method for the preparation of oligonucleotides containing internally-attached galactose and triantennary galactose units has been developed based on click chemistry between 2′-N-alkyne 2′-amino-LNA nucleosides and azido-functionalized galactosyl building blocks. The synthesized oligonucleotides show excellent binding affinity and selectivity towards complementary DNA/RNA strands with an

  基于 2'-N-炔烃 2'-氨基-LNA 核苷和叠氮基功能化的半乳糖基结构单元之间的点击化学，开发了一种制备含有内部连接的半乳​​糖和三触角半乳糖单元的寡核苷酸的便捷方法。合成的寡核苷酸对互补 DNA/RNA 链显示出优异的结合亲和力和选择性，三重修饰变体的解链温度最高可提高 +23.5 °C。