N-(2[2-[2-azidoethoxy]ethoxy]ethoxy)phthalimide | 1374225-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(2[2-[2-azidoethoxy]ethoxy]ethoxy)phthalimide
• CAS: 1374225-43-0
• 化学式: C₁₄H₁₆N₄O₅
• 分子量: 320.305
• InChiKey: VSOYVRCLZMPVRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  23.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  113.83
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(2[2-[2-azidoethoxy]ethoxy]ethoxy)phthalimide 在 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 氨氧基-二聚乙二醇-叠氮
  参考文献：
  名称：

  Site-Selective Glycosylation of Hemoglobin with Variable Molecular Weight Oligosaccharides: Potential Alternative to PEGylation

  摘要：

  Poly(ethylene glycol) (PEG) conjugation (i.e., PEGylatiori) is a commonly used strategy to increase the circulatory half-life of therapeutic proteins and colloids; however, few viable alternatives exist to replicate its functions. Herein, we report a method for the rapid site-selective glycosylation of proteins with variously sized carbohydrates, up to a molecular weight (MW) of 10 000, thus serving as a potential alternative for PEGylation. More importantly, the method developed has two unique features. First, traditional protecting group strategies that typically accompany the modification of the carbohydrate fragments are circumvented, allowing for the facile site-selective glycosylation of a desired protein with variously sized glycans. Second, the methodology employed is not limited by oligosaccharide size; consequently, glycans of MW similar to that of PEG, used in the PEGylation of therapeutic proteins, can be employed. To demonstrate the usefulness of this technology, hemoglobin (Hb) was site-selectively glycosylated with a series of carbohydrates of increasing MW (from 504 to similar to 10 000). Hb was selected on the basis of the vast wealth of biochemical and biophysical knowledge present in the literature and because of its use as a precursor in the synthesis/formulation of artificial red blood cell substitutes. Following the successful site-selective glycosylation of Hb, the impact of increasing the glycan MW on Hb's biophysical properties was investigated in vitro.

  DOI：

  10.1021/ja300893t
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 在 sodium azide 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 N-(2[2-[2-azidoethoxy]ethoxy]ethoxy)phthalimide
  参考文献：
  名称：

  Site-Selective Glycosylation of Hemoglobin with Variable Molecular Weight Oligosaccharides: Potential Alternative to PEGylation

  摘要：

  Poly(ethylene glycol) (PEG) conjugation (i.e., PEGylatiori) is a commonly used strategy to increase the circulatory half-life of therapeutic proteins and colloids; however, few viable alternatives exist to replicate its functions. Herein, we report a method for the rapid site-selective glycosylation of proteins with variously sized carbohydrates, up to a molecular weight (MW) of 10 000, thus serving as a potential alternative for PEGylation. More importantly, the method developed has two unique features. First, traditional protecting group strategies that typically accompany the modification of the carbohydrate fragments are circumvented, allowing for the facile site-selective glycosylation of a desired protein with variously sized glycans. Second, the methodology employed is not limited by oligosaccharide size; consequently, glycans of MW similar to that of PEG, used in the PEGylation of therapeutic proteins, can be employed. To demonstrate the usefulness of this technology, hemoglobin (Hb) was site-selectively glycosylated with a series of carbohydrates of increasing MW (from 504 to similar to 10 000). Hb was selected on the basis of the vast wealth of biochemical and biophysical knowledge present in the literature and because of its use as a precursor in the synthesis/formulation of artificial red blood cell substitutes. Following the successful site-selective glycosylation of Hb, the impact of increasing the glycan MW on Hb's biophysical properties was investigated in vitro.

  DOI：

  10.1021/ja300893t