N-acetyl-beta-D-galactosamine | 14131-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetyl-beta-D-galactosamine
• 英文别名: 2-acetamido-2-deoxy-β-D-galactopyranoside；2-acetamido-2-deoxy-β-D-galactopyranose；2-acetamido-2-deoxy-β-D-galactose；N-acetyl-β-D-galactosamine；N-Acetyl D-galactosamine；beta-N-ACETYL-D-GALACTOSAMINE；N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 14131-60-3
• 化学式: C₈H₁₅NO₆
• 分子量: 221.21
• InChiKey: OVRNDRQMDRJTHS-JAJWTYFOSA-N

物化性质

• 沸点：
  595.4±50.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-acetyl-beta-D-galactosamine 在 吡啶 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 生成 2-acetamido-4,6-O-benzylidene-2-deoxy-1,3-di-O-acetyl-α-D-galactopyranose
  参考文献：
  名称：

  Jiaang, Weir-Torn; Tseng, Ping-Hui; Chen, Shui-Tein, Synlett, 2000, # 6, p. 797 - 800

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-Alpha-D-吡喃糖 在 吡啶 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 85.25h， 生成 N-acetyl-beta-D-galactosamine
  参考文献：
  名称：

  Conversion of 2-acetamido-2-deoxy-β-D-glucopyranose (N-acetylglucosamine) into 2-acetamido-2-deoxy-β-D-galactopyranose (N-acetylgalactosamine) using a biotransformation to generate a selectively deprotected substrate for S_N2 inversion

  摘要：

  A procedure is described for the conversion of N-acetylglucosamine 2 into N-acetylgalactosamine 1, in which use is made of a 4,6-acetyl migration in a precursor selectively deprotected by a biotransformation procedure.

  DOI：

  10.1039/p19920000235

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。
• A stereoselective and flexible synthesis to access both enantiomers of <i>N</i>-acetylgalactosamine and peracetylated <i>N</i>-acetylidosamine
  作者：Bettina Riedl、Walther Schmid

  DOI：10.3762/bjoc.14.71

  日期：——

  the Pd-catalyzed, stereo- and regioselective epoxide opening and subsequent nucleophilic substitution of an azide functionality. This approach enables the synthesis of the naturally D- and unnaturally L-configured GalNAc, as well as both enantiomers of the largely unknown N-acetylidosamine (IdoNAc).

  合成N-乙酰半乳糖胺（GalNAc）的方法引起了极大的兴趣，因为该化合物在细胞间相互作用和受体诱导的细胞信号转导中起着举足轻重的作用。在本文中，我们提出了一种合成途径，其中目标化合物中存在的四个立体异构中心中的两个源自对映体纯的酒石酸，后者被选择性地转化为环氧醇。关键步骤是Pd催化的立体和区域选择性环氧化物的开环以及随后叠氮化物官能团的亲核取代。该方法能够合成天然D-和非天然L-构型的GalNAc，以及在很大程度上未知的N-乙酰氨基胺（IdoNAc）的两种对映异构体。
• [EN] siRNAs WITH AT LEAST TWO LIGANDS AT DIFFERENT ENDS<br/>[FR] ARNSI POSSÉDANT AU MOINS DEUX LIGANDS À DEUX EXTRÉMITÉS DISTINCTES
  申请人：SILENCE THERAPEUTICS GMBH

  公开号：WO2019193189A1

  公开（公告）日：2019-10-10

  There is provided inter alia a conjugate for inhibiting expression of a target gene in a cell, said conjugate comprising a nucleic acid portion and ligand portions, said nucleic acid portion comprising at least one duplex region that comprises at least a portion of a first RNA strand and at least a portion of a second RNA strand that is at least partially complementary to the first strand, wherein said first strand is at least partially complementary to at least a portion of RNA transcribed from said target gene, said ligand portions comprising a linker moiety and a targeting ligand for in vivo targeting of cells and being conjugated exclusively to the 3' and/or 5' ends of one or both RNA strands, wherein the 5' end of the first RNA strand is not conjugated, wherein: (i) the second RNA strand is conjugated at the 5' end to the targeting ligand, and wherein (a) the second RNA strand is also conjugated at the 3' end to the targeting ligand and the 3' end of the first RNA strand is not conjugated; or (b) the first RNA strand is conjugated at the 3' end to the targeting ligand and the 3' end of the second RNA strand is not conjugated; or (c) both the second RNA strand and the first RNA strand are also conjugated at the 3' ends to the targeting ligand; or (ii) both the second RNA strand and the first RNA strand are conjugated at the 3' ends to the targeting ligand and the 5' end of the second RNA strand is not conjugated.

  提供了一种用于抑制细胞中靶基因表达的共轭物，该共轭物包括核酸部分和配体部分，所述核酸部分包括至少一个双链区域，该区域包括至少部分第一RNA链和至少部分第二RNA链，该第二RNA链至少部分与第一链互补，其中所述第一链至少部分与从所述靶基因转录的RNA的至少部分互补，所述配体部分包括连接子基团和用于体内细胞靶向的靶向配体，并且仅连接到一个或两个RNA链的3'和/或5'末端，其中第一RNA链的5'末端未连接，其中：(i) 第二RNA链在5'末端连接到靶向配体，其中(a) 第二RNA链还在3'末端连接到靶向配体，且第一RNA链的3'末端未连接；或(b) 第一RNA链在3'末端连接到靶向配体，且第二RNA链的3'末端未连接；或(c) 第二RNA链和第一RNA链的3'末端均连接到靶向配体；或(ii) 第二RNA链和第一RNA链的3'末端均连接到靶向配体，且第二RNA链的5'末端未连接。
• One-Pot Synthesis of Unprotected Anomeric Glycosyl Thiols in Water for Glycan Ligation Reactions with Highly Functionalized Sugars
  作者：Sebastian Köhling、Matthias P. Exner、Saba Nojoumi、Jürgen Schiller、Nediljko Budisa、Jörg Rademann

  DOI：10.1002/anie.201607228

  日期：2016.12.12

  Chemical synthesis of oligosaccharide conjugates is essential for studying the functional relevance of carbohydrates, and this task would be facilitated considerably if reliable methods for the anomeric ligation of unprotected sugars in water were available. Here, a method for the preparation of anomeric glycosyl thiols from complex unprotected mono‐, di‐, and oligosaccharides is presented. By exploiting

  寡糖缀合物的化学合成对于研究碳水化合物的功能相关性至关重要，如果可以使用可靠的方法将水中未保护的糖进行异头连接，则将大大简化此任务。本文介绍了一种从复杂的未保护的单糖，二糖和寡糖制备异头糖基硫醇的方法。通过利用2-乙酰氨基基团的邻近基团效应，可以生成1,2-恶唑啉，并通过用1-硫代酸处理将其转化为1-糖基硫代酯。原位释放的未保护的异头糖基硫醇盐与迈克尔受体，脂族卤化物和氮丙啶偶联，以提供通用的糖偶联物。氨基酸和蛋白质的缀合是通过硫醇与末端烯烃的反应完成的。
• [EN] NOVEL TETRAGALNAC CONTAINING CONJUGATES AND METHODS FOR DELIVERY OF OLIGONUCLEOTIDES<br/>[FR] NOUVEAUX CONJUGUÉS CONTENANT TÉTRAGALNAC ET PROCÉDÉS POUR L'ADMINISTRATION D'OLIGONUCLÉOTIDES
  申请人：MERCK SHARP & DOHME

  公开号：WO2013166121A1

  公开（公告）日：2013-11-07

  Disclosed herein is a modular composition comprising 1) an oligonucleotide; 2) one or more tetraGalNAc ligands of Formula (I), which may be the same or different; optionally, 3) one or more linkers, which may be the same or different; and optionally, 4) one or more targeting ligands, solubilizing agents, pharmacokinetics enhancing agents, lipids, and/or masking agents.

  本文揭示了一种模块化组合物，包括1）寡核苷酸；2）一个或多个Formula (I)的四聚GalNAc配体，可能相同或不同；可选地，3）一个或多个连接剂，可能相同或不同；以及可选地，4）一个或多个靶向配体、增溶剂、药代动力学增强剂、脂质和/或掩蔽剂。