β-methyl-2-amino-2,3-didesoxy-D-ribofuranoside | 689221-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: β-methyl-2-amino-2,3-didesoxy-D-ribofuranoside
• 英文别名: [(2S,4R,5R)-4-amino-5-methoxyoxolan-2-yl]methanol
• CAS: 689221-47-4
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: MFVYVHRHDVRWQK-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  β-methyl-2-amino-2,3-didesoxy-D-ribofuranoside 在 苯磺酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 生成
  参考文献：
  名称：

  Structural modifications of antisense oligonucleotides

  摘要：

  Antisense oligonucleotides are efficient tools for the inhibition of gene expression in a sequence specific way. Natural oligonucleotides are decomposed rapidly in biological systems, which strongly restrict their application. In contrast, artificial oligonucleotides are designed to be more stable against degradation than the target mRNA, which results in a catalytic effect of the drug. Modification of the phosphate linkage has been the first successful strategy for antisense drug developments and Fomivirsene the first antisense drug in therapy. The launch of Fomivirsene has resulted in a revolutionary spin off to antisense research leading to a second generation of antisense oligonucleotides, which are stable against oligonucleotide cleaving enzymes. Among these, oligonucleotides bearing an alkoxy substituent in position 2' were the most successful ones. The third generation of antisense oligonucleotides contains structure elements, which enhance the antisense action. Zwitterionic oligonucleotides show remarkable results, first, because the stability against ribozymes is largely increased, and secondly, because the electrostatic repulsion between the anionic sense and the zwitterionic antisense cords is minimized. Promising new target molecules in antisense research are oligonucleotide chimäres, which enhance the antisense action (chimäres with intercalators, chelators or polyamines) or enable an application as sequence specific detectors (chimäres with biotin, fluorescein or radioligands).

  DOI：

  10.1016/s0014-827x(03)00022-3
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 palladium on activated charcoal 咪唑 、 sodium periodate 、 lithium aluminium tetrahydride 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 氢气 、 三正丁基氢锡 、 sodium methylate 、 三氯化铁 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 20.0 ℃ 、400.0 kPa 条件下， 反应 77.5h， 生成 β-methyl-2-amino-2,3-didesoxy-D-ribofuranoside
  参考文献：
  名称：

  ?-Methyl-2-amino-2,3-didesoxyribofuranoside, a Novel Building Block for Backbone Modified Antisense Oligonucleotides

  摘要：

  A synthesis of the amino sugar 2-amino-2,3-didesoxyribose is described. Starting from D-glucosamine, beta-methylfuranoside was obtained in eight steps in 20% yield. This carbohydrate is a novel building block for nucleosides and for backbone modified antisense oligonucleotides with 2'-5' amide linkages.

  DOI：

  10.1007/s00706-003-0086-1

文献信息

• ?-Methyl-2-amino-2,3-didesoxyribofuranoside, a Novel Building Block for Backbone Modified Antisense Oligonucleotides
  作者：Johannes Winkler、Ernst Urban、Christian R. Noe

  DOI：10.1007/s00706-003-0086-1

  日期：2004.1.1

  A synthesis of the amino sugar 2-amino-2,3-didesoxyribose is described. Starting from D-glucosamine, beta-methylfuranoside was obtained in eight steps in 20% yield. This carbohydrate is a novel building block for nucleosides and for backbone modified antisense oligonucleotides with 2'-5' amide linkages.
• Structural modifications of antisense oligonucleotides
  作者：Ernst Urban、Christian R. Noe

  DOI：10.1016/s0014-827x(03)00022-3

  日期：2003.3

  Antisense oligonucleotides are efficient tools for the inhibition of gene expression in a sequence specific way. Natural oligonucleotides are decomposed rapidly in biological systems, which strongly restrict their application. In contrast, artificial oligonucleotides are designed to be more stable against degradation than the target mRNA, which results in a catalytic effect of the drug. Modification of the phosphate linkage has been the first successful strategy for antisense drug developments and Fomivirsene the first antisense drug in therapy. The launch of Fomivirsene has resulted in a revolutionary spin off to antisense research leading to a second generation of antisense oligonucleotides, which are stable against oligonucleotide cleaving enzymes. Among these, oligonucleotides bearing an alkoxy substituent in position 2' were the most successful ones. The third generation of antisense oligonucleotides contains structure elements, which enhance the antisense action. Zwitterionic oligonucleotides show remarkable results, first, because the stability against ribozymes is largely increased, and secondly, because the electrostatic repulsion between the anionic sense and the zwitterionic antisense cords is minimized. Promising new target molecules in antisense research are oligonucleotide chimäres, which enhance the antisense action (chimäres with intercalators, chelators or polyamines) or enable an application as sequence specific detectors (chimäres with biotin, fluorescein or radioligands).