azidopropyl 2,3,4-tri-O-acetyl-β-Lfucose | 1202384-47-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: azidopropyl 2,3,4-tri-O-acetyl-β-Lfucose
• CAS: 1202384-47-1
• 化学式: C₁₅H₂₃N₃O₈
• 分子量: 373.363
• InChiKey: CGKPLKKAPOITEL-KVOGPGQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  146.12
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  azidopropyl 2,3,4-tri-O-acetyl-β-Lfucose 在 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Lipoic Acid Glyco-Conjugates, a New Class of Agents for Controlling Nonspecific Adsorption of Blood Serum at Biointerfaces for Biosensor and Biomedical Applications

  摘要：

  The carbohydrate-derived lipoic acid derivatives were Studied as protein and cell resistant biomaterials. Six types of carbohydrates were examined for their abilities to reduce nonspecific adsorption of human serum and Hela cell using quartz crystal microbalance. Our data Suggested that the Structures of carbohydrates play an important role in resisting nonspecific binding. Specifically, the resistance was found to increase in the order lipoic fucose < lipoic mannose < lipoic N-acetyl glucosamine < lipoic glucose < lipoic sialic acid < lipoic galactose, where lipoic galactose derivative resisted most nonspecific adsorption. Furthermore, the combination of lipoic galactose and BSA was the most effective in reducing the adsorption of even undiluted human serum and the attachment of Hela cells while allowing specific binding. Several control experiments have demonstrated that the resistant-ability of mixed lipoic galactose and BSA was comparable to the best known system for decreasing nonspecific adsorption.

  DOI：

  10.1021/la903261j
• 作为产物：
  描述：

  bromopropyl 2,3,4-tri-O-acetyl-β-Lfucose 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以97%的产率得到azidopropyl 2,3,4-tri-O-acetyl-β-Lfucose
  参考文献：
  名称：

  Magnetic Glyco-Nanoparticles: A Tool To Detect, Differentiate, and Unlock the Glyco-Codes of Cancer via Magnetic Resonance Imaging

  摘要：

  Within cancer, there is a large wealth of diversity, complexity, and information that nature has engineered rendering it challenging to identify reliable detection methods. Therefore, the development of simple and effective techniques to delineate the fine characteristics of cancer cells can have great potential impacts on cancer diagnosis and treatment. Herein, we report a magnetic glyco-nanoparticle (MGNP) based nanosensor system bearing carbohydrates as the ligands, not only to detect and differentiate cancer cells but also to quantitatively profile their carbohydrate binding abilities by magnetic resonance imaging (MRI). Using an array of MGNPs, a range of cells including closely related isogenic tumor cells, cells with different metastatic potential and malignant vs normal cells can be readily distinguished based on their respective "MRI signatures". Furthermore, the information obtained from such studies helped guide the establishment of strongly binding MGNPs as antiadhesive agents against tumors. As the interactions between glycoconjugates and endogenous lectins present on cancer cell surface are crucial for cancer development and metastasis, the ability to characterize and unlock the glyco-code of individual cell lines can facilitate both the understanding of the roles of carbohydrates as well as the expansion of diagnostic and therapeutic tools for cancer.

  DOI：

  10.1021/ja100455c