O(2)-(3,4,6-tri-O-acetyl-N-acetyl-β-D-glucosaminyl) 1-[N-(2-hydroxyethyl)-N-methylamino]diazen-1-ium-1,2-diolate | 1202358-00-6

• 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: O(2)-(3,4,6-tri-O-acetyl-N-acetyl-β-D-glucosaminyl) 1-[N-(2-hydroxyethyl)-N-methylamino]diazen-1-ium-1,2-diolate
• 英文别名: RN-2-21
• CAS: 1202358-00-6
• 化学式: C₁₇H₂₈N₄O₁₁
• 分子量: 464.43
• InChiKey: KXWDMIQGFQJATL-HHARLNAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.62
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  188.36
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  O(2)-(3,4,6-tri-O-acetyl-N-acetyl-β-D-glucosaminyl) 1-[N-(2-hydroxyethyl)-N-methylamino]diazen-1-ium-1,2-diolate 在 sodium periodate 、 ruthenium(III) chloride trihydrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以54%的产率得到O(2)-(3,4,6-tri-O-acetyl-N-acetyl-β-D-glucosaminyl) 1-[N-(2-carboxymethyl)-N-methylamino]diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  Glycosylated PROLI/NO Derivatives as Nitric Oxide Prodrugs

  摘要：

  GlcNAc-PROLI/NO prodrugs that are activated by N-acetylglucosaminidase to release nitric oxide (NO) are described. A classical acid-amine coupling is used to bifunctionalize these PROLI/NO prodrugs, which on activation generate up to 4 mol of NO, a peptide residue, and an N-acetylglucosamine residue. Many of the prodrugs synthesized are efficient sources of intracellular NO.

  DOI：

  10.1021/ol902481s
• 作为产物：
  描述：

  1-hydroxy-[3-(2-hydroxyethyl)-3-methyl]-1-triazene 2-oxide sodium salt 、 1-chloro-N-acetylglucosamine triacetate 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 以35%的产率得到O(2)-(3,4,6-tri-O-acetyl-N-acetyl-β-D-glucosaminyl) 1-[N-(2-hydroxyethyl)-N-methylamino]diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  Glycosylated PROLI/NO Derivatives as Nitric Oxide Prodrugs

  摘要：

  GlcNAc-PROLI/NO prodrugs that are activated by N-acetylglucosaminidase to release nitric oxide (NO) are described. A classical acid-amine coupling is used to bifunctionalize these PROLI/NO prodrugs, which on activation generate up to 4 mol of NO, a peptide residue, and an N-acetylglucosamine residue. Many of the prodrugs synthesized are efficient sources of intracellular NO.

  DOI：

  10.1021/ol902481s