1-(2'-acetamido-2'-deoxy-α-D-galactopyranosyl)-2-propene | 271246-14-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2'-acetamido-2'-deoxy-α-D-galactopyranosyl)-2-propene
• 英文别名: N-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-prop-2-enyloxan-3-yl]acetamide
• CAS: 271246-14-1
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: PWFYUSQMOZEDLN-SAVGLBRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2'-acetamido-2'-deoxy-α-D-galactopyranosyl)-2-propene 在 吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 [(2R,3R,4R,5S,6R)-5-acetamido-3,4-diacetyloxy-6-(2-oxoethyl)oxan-2-yl]methyl acetate
  参考文献：
  名称：

  [EN] OLIGONUCLEOTIDE-LIGAND CONJUGATES AND PROCESS FOR THEIR PREPARATION
  [FR] CONJUGUÉS LIGANDS D'OLIGONUCLÉOTIDES ET PROCÉDÉ POUR LEUR PRÉPARATION

  摘要：

  公开号：

  WO2015006740A3
• 作为产物：
  描述：

  1-(2'-acetamido-2'-deoxy-α-D-glucopyranosyl)-2-propene 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 三氟甲磺酸酐 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 生成 1-(2'-acetamido-2'-deoxy-α-D-galactopyranosyl)-2-propene
  参考文献：
  名称：

  [EN] OLIGONUCLEOTIDE-LIGAND CONJUGATES AND PROCESS FOR THEIR PREPARATION
  [FR] CONJUGUÉS LIGANDS D'OLIGONUCLÉOTIDES ET PROCÉDÉ POUR LEUR PRÉPARATION

  摘要：

  公开号：

  WO2015006740A3

文献信息

• NEOGLYCOCONJUGATES AS VACCINES AND THERAPEUTIC TOOLS
  申请人：KORANEX CAPITAL

  公开号：US20210085770A1

  公开（公告）日：2021-03-25

  Neoglycoconjugates as immunogens and therapeutic/diagnostic tools are described herein. The neoglycoconjugates are produced by conjugating a carbohydrate antigen intermediate to a free amine group of a carrier material (e.g., carrier protein). The intermediate comprises a linker having a first end and a second end, the first end being conjugated to a carbohydrate antigen via a thio ether bond and the second end comprising a functional group reactable with a free amine group. Following coupling, the carbohydrate antigen becomes covalently bound to the carrier material via an amide, a carbamate, a sulfonamide, a urea, or a thiourea bond, thereby producing the neoglycoconjugate. Applications of the neoglycoconjugates as antigens, immunogens, vaccines, and in diagnostics are also described. Specifically, the use of (neo)glycoconjugates as vaccine candidates and other therapeutic tools against cancers, viruses such as SARS-CoV-2, and other diseases characterized by expression of aberrant glycosylation are also described.

  新糖基共轭物作为免疫原和治疗/诊断工具在此进行描述。这些新糖基共轭物是通过将碳水化合物抗原中间体与载体材料（例如载体蛋白质）的自由胺基结合而产生的。该中间体包括具有第一端和第二端的连接物，第一端通过硫醚键与碳水化合物抗原结合，第二端包括可与自由胺基反应的功能基团。在偶联后，碳水化合物抗原通过酰胺、碳酸酯、磺酰胺、脲或硫脲键与载体材料共价结合，从而产生新糖基共轭物。还描述了将新糖基共轭物用作抗原、免疫原、疫苗和诊断的应用。具体地，还描述了将（新）糖基共轭物用作疫苗候选物和其他治疗工具，用于对抗癌症、冠状病毒（例如SARS-CoV-2）等病毒以及其他表达异常糖基化的疾病。
• Synthesis of Double <i>C</i>-Glycoside Analogue of sTn
  作者：Dino K. Ress、Sultan N. Baytas、Qun Wang、Eva M. Muñoz、Kazuo Tokuzoki、Hiroshi Tomiyama、Robert J. Linhardt

  DOI：10.1021/jo050691n

  日期：2005.9.1

  A sTn double C-glycoside, sTn analogue 2, was synthesized using samarium chemistry developed in our laboratory. Complications in the oxidation reaction affording aldehyde acceptor were overcome by double protection of amide and the use of a room-temperature ionic liquid as solvent. Studies are underway to conjugate the sTn double C-glycoside hapten 2 to KLH carrier protein for biological evaluation

  使用我们实验室开发的钐化学合成了 sTn 双C -糖苷，sTn 类似物2 。通过酰胺的双重保护和使用室温离子液体作为溶剂克服了提供醛受体的氧化反应中的复杂性。正在进行研究将 sTn 双C-糖苷半抗原2与 KLH 载体蛋白缀合，以作为疫苗进行生物学评估。
• Precision glycoconjugates as therapeutic tools
  申请人：KORANEX CAPITAL

  公开号：US10610576B2

  公开（公告）日：2020-04-07

  The present description relates to glycoconjugates, glycoconjugate immunogens and glycoconjugate vaccines comprising carbohydrate antigens coupled to immunogenic carrier proteins, or materials used for detection and screening of resulting antibodies. Improved methods of more directly and precisely conjugating carbohydrate antigens to free thiol groups of immunogenic carrier proteins are described, including “click-chemistry” approaches based on photocatalytic thiol-ene reactions.

  本说明涉及糖结合物、糖结合免疫原和糖结合疫苗，包括与免疫原载体蛋白偶联的碳水化合物抗原，或用于检测和筛选由此产生的抗体的材料。本文介绍了更直接、更精确地将碳水化合物抗原与免疫原载体蛋白的游离硫醇基团偶联的改进方法，包括基于光催化硫醇-烯反应的 "点击化学 "方法。
• Neoglycoconjugates as vaccines and therapeutic tools
  申请人：KORANEX CAPITAL

  公开号：US10973910B1

  公开（公告）日：2021-04-13

  Neoglycoconjugates as immunogens and therapeutic/diagnostic tools are described herein. The neoglycoconjugates are produced by conjugating a carbohydrate antigen intermediate to a free amine group of a carrier material (e.g., carrier protein). The intermediate comprises a linker having a first end and a second end, the first end being conjugated to a carbohydrate antigen via a thio ether bond and the second end comprising a functional group reactable with a free amine group. Following coupling, the carbohydrate antigen becomes covalently bound to the carrier material via an amide, a carbamate, a sulfonamide, a urea, or a thiourea bond, thereby producing the neoglycoconjugate. Applications of the neoglycoconjugates as antigens, immunogens, vaccines, and in diagnostics are also described. Specifically, the use of (neo)glycoconjugates as vaccine candidates and other therapeutic tools against cancers, viruses such as SARS-CoV-2, and other diseases characterized by expression of aberrant glycosylation are also described.

  本文介绍了作为免疫原和治疗/诊断工具的新糖蛋白轭合物。新甘油三酯是通过将碳水化合物抗原中间体与载体材料（如载体蛋白）的游离胺基团共轭而制成的。中间体包括具有第一端和第二端的连接体，第一端通过硫醚键与碳水化合物抗原连接，第二端包括可与游离胺基团反应的官能团。偶联后，碳水化合物抗原通过酰胺键、氨基甲酸酯键、磺酰胺键、脲键或硫脲键与载体材料共价结合，从而产生新甘糖共轭物。此外，还介绍了新甘氨酸轭合物作为抗原、免疫原、疫苗以及在诊断中的应用。具体而言，还介绍了（新）糖轭合物作为候选疫苗和其他治疗工具，用于抗击癌症、SARS-CoV-2 等病毒以及以表达异常糖基化为特征的其他疾病。
• Stereoselective synthesis of α-C-glycosides of N-acetylgalactosamine
  作者：Laura Cipolla、Barbara La Ferla、Luigi Lay、Francesco Peri、Francesco Nicotra

  DOI：10.1016/s0957-4166(99)00480-2

  日期：2000.1

  Attempts to synthesise alpha-C-glycosides of N-acetylgalactosamine by selective deprotection at C-2' of allyl alpha-C-galactoside 1 and subsequent amination failed, but opened the way to alpha-C-talopyranosides. The synthesis of alpha-C-glycosides of N-acetylgalactosamine was performed from allyl alpha-C-glucopyranoside 9, which was regioselectively deprotected, stereoselectively aminated at C-2', and finally epimerised at C-4'. (C) 2000 Elsevier Science Ltd. All rights reserved.