epi-5-(3-aminopropyl)-amino-1,3,2',6'-tetraazido neamine | 948916-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: epi-5-(3-aminopropyl)-amino-1,3,2',6'-tetraazido neamine
• 英文别名: (2R,3S,4R,5R,6S)-6-[(1S,2S,3R,4R,6S)-2-(3-aminopropylamino)-4,6-diazido-3-hydroxycyclohexyl]oxy-5-azido-2-(azidomethyl)oxane-3,4-diol
• CAS: 948916-01-6
• 化学式: C₁₅H₂₆N₁₄O₅
• 分子量: 482.462
• InChiKey: NWVWFOWKKMPJTF-ZTIGNSIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  175
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  epi-5-(3-aminopropyl)-amino-1,3,2',6'-tetraazido neamine 在 硫化氢 、 potassium carbonate 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 甲醇 、 水 、 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Synthesis of aminodisaccharide–nucleoside conjugates for RNA binding

  摘要：

  Two types of aminodisaccharide-nucleoside conjugates were synthesized by the condensation of azidodisaccharide and nucleoside using aliphatic diamine as a linker. The corresponding azidodisaccharides could be yielded from neamine in good yield. The binding properties to 16S RNA of these conjugates were evaluated by SPR. It was found that the nucleobase played a significant role in the binding of these conjugates to 16S RNA and a shorter linker between the aminodisaccharide and nucleoside was favorable for 16S RNA binding. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.002
• 作为产物：
  描述：

  三氟甲磺酸酐 、 1,3-丙二胺 、 3',4',6-tri-O-acetyl-1,3,2',6'-tetrazidoneamine 以 吡啶 、 二氯甲烷 、 四氢呋喃 为溶剂， 反应 25.5h， 以60%的产率得到epi-5-(3-aminopropyl)-amino-1,3,2',6'-tetraazido neamine
  参考文献：
  名称：

  Synthesis of aminodisaccharide–nucleoside conjugates for RNA binding

  摘要：

  Two types of aminodisaccharide-nucleoside conjugates were synthesized by the condensation of azidodisaccharide and nucleoside using aliphatic diamine as a linker. The corresponding azidodisaccharides could be yielded from neamine in good yield. The binding properties to 16S RNA of these conjugates were evaluated by SPR. It was found that the nucleobase played a significant role in the binding of these conjugates to 16S RNA and a shorter linker between the aminodisaccharide and nucleoside was favorable for 16S RNA binding. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.002

文献信息

• Studies on the synthesis of neamine-dinucleosides and neamine-PNA conjugates and their interaction with RNA
  作者：Hui Mei、Lei Xing、Li Cai、Hong-Wei Jin、Peng Zhao、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1016/j.bmcl.2008.09.062

  日期：2008.10

  neamine-dinucleotide conjugates 8a-g and neamine-PNA conjugates 12a-c and 14a-d, were synthesized. Compound 8a-g were synthesized by the condensation of azido-neamine with dinucleotide-5'-carboxylic acids, followed by reduction and deprotection. Compound 12a-c and 14a-d were synthesized by the similar strategy. The binding affinities of conjugates 8a-g, 12a-c, and 14a-d towards 16S RNA, 18S RNA, and TAR RNA were evaluated

  合成了两种类型的神经胺衍生物，即神经胺-二核苷酸缀合物8a-g和神经胺-PNA缀合物12a-c和14a-d。通过叠氮基-亚胺与二核苷酸-5'-羧酸的缩合，然后还原和脱保护，来合成化合物8a-g。通过相似的策略合成化合物12a-c和14a-d。通过SPR评估缀合物8a-g，12a-c和14a-d对16S RNA，18S RNA和TAR RNA的结合亲和力。这表明缀合物12a-c和14a-d以与神经胺相同的水平与16S，18S RNA相互作用，与神经胺相比，14a和14d显示出对TAR RNA的约两倍的结合亲和力。但是，神经胺二核苷酸共轭物8a-g对16S，18S和TAR RNA的结合亲和力很弱，