5'-amino-5'-deoxy-2'-O-methyladenosine | 251296-68-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-amino-5'-deoxy-2'-O-methyladenosine
• 英文别名: (2R,3R,4R,5R)-2-(aminomethyl)-5-(6-aminopurin-9-yl)-4-methoxyoxolan-3-ol
• CAS: 251296-68-1
• 化学式: C₁₁H₁₆N₆O₃
• 分子量: 280.286
• InChiKey: OWCFSQWJGFULOS-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-amino-5'-deoxy-2'-O-methyladenosine 、 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-[[(4-nitrophenoxy)carbonyl]methyl]uridine 以 四氢呋喃 、 乙醇 为溶剂， 反应 120.0h， 以74%的产率得到2'-O-(tert-butyldimethylsilyl)-3'-deoxy-5'-O-(4,4-dimethoxytrityl)-3'-[[N-(2'-O-methyl-5'-deoxyadenosin-5'-yl)carbamoyl]methyl]uridine
  参考文献：
  名称：

  Amide-Linked Ribonucleoside Dimers Derived from 5‘-Amino-5‘-deoxy- and 3‘-(Carboxymethyl)-3‘-deoxynucleoside Precursors¹

  摘要：

  Treatment of tert-butyldimethylsilyl (TBDMS) derivatives of 3'-keto(adenosine or uridine) with [(ethoxycarbonyl)methylene]triphenylphosphorane gave exocyclic alkenes that underwent stereoselective hydrogenation to give 3'-deoxy-3'-[(ethoxycarbonyl)methyl](Ado or Urd) analogues. Saponification provided the 3'-(carboxymethyl)-3'-deoxy(Ado and Urd) derivatives 37 and 38. Treatment of 37 or 38 with DCC and 5'-amino-2',3'-bis-O-TBDMS-5'-deoxynucleosides gave the amide-linked dimers (74-82%). Activation of 37 or 38 with 4-nitrophenol/DCC, and direct coupling of the 4-nitrophenyl esters with 5'-amino-5'-deoxy(Ado or Urd) in pyridine also produced amide dimers efficiently (65-70%). Analogous activation of a 5'-O-DMT-protected carboxylate, and its coupling with 5'-amino-5'-deoxy-2'-O-methyladenosine gave the amide dimer in good yield (74%). Coupling (DCC) of a 5'-azido-2'-O-TBDMS-3'-(carboxymethyl)-3', 5'-dideoxyuridine intermediate with 5'-amino-5'-deoxynucleosides gave amide-linked dimers (72-78%) that can serve as masked (azide reduction) 5'-amino dimers for analogous synthesis of extended amide-linked oligomers.

  DOI：

  10.1021/jo9908647
• 作为产物：
  描述：

  2'-O-甲基腺苷 在 palladium on activated charcoal 氯化亚砜 、 sodium azide 、 氢气 作用下， 以 六甲基磷酰三胺 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5'-amino-5'-deoxy-2'-O-methyladenosine
  参考文献：
  名称：

  小寡核苷酸的酰胺连接的[（3'）CH2CO-NH（5'）]核苷类似物的合成。

  摘要：

  我们报告了反义寡核苷酸组件的新的酰胺连接的（二戊）核苷类似物的合成。3'-（羧甲基）-3'-脱氧-和5'-氨基-5'-脱氧核苷衍生物的溶液相偶联提供了酰胺二聚体。具有5'-叠氮基-5'-脱氧功能的活化的[3'-（羧甲基）-3'-脱氧]单元提供“被屏蔽的” 5'-氨基-5'-脱氧残基用于链延伸，以及5'- O-DMT保护的单元提供了5'末端以连接至磷酸二酯键。

  DOI：

  10.1080/15257770008032997

文献信息

• Enzymatic nucleic acids containing 5'-and/or 3'-cap structures
  申请人：Matulic-Adamic Jasenka

  公开号：US20050074760A1

  公开（公告）日：2005-04-07

  An enzymatic nucleic acid molecule comprising a 5′- and/or a 3′-cap structure, wherein said structure is not a 5′-5′-linked inverted nucleotide or a 3′-3′-linked inverted nucleotide.

  一种酶性核酸分子，包括5'-和/或3'-端帽结构，其中所述结构不是5'-5'-连接的反向核苷酸或3'-3'-连接的反向核苷酸。
• Synthesis of methoxy nucleosides and enzymatic nucleic acid molecules
  申请人：RIBOZYME PHARMACEUTICALS, INC.

  公开号：EP1108724A2

  公开（公告）日：2001-06-20

  This invention relates to chemical synthesis of 2'-O-methyl, 3'-O-methyl and 5'-O-methyl nucleosides, incorporation of novel chemical modifications in enzymatic nucleic acid molecules and improved methods for the synthesis of enzymatic nucleic acid molecules.

  本发明涉及 2'-O-甲基、3'-O-甲基和 5'-O-甲基核苷的化学合成、在酶核酸分子中加入新型化学修饰以及改进酶核酸分子的合成方法。
• US5998203A
  申请人：——

  公开号：US5998203A

  公开（公告）日：1999-12-07
• US6586238B1
  申请人：——

  公开号：US6586238B1

  公开（公告）日：2003-07-01
• Amide-Linked Ribonucleoside Dimers Derived from 5‘-Amino-5‘-deoxy- and 3‘-(Carboxymethyl)-3‘-deoxynucleoside Precursors¹
  作者：Matt A. Peterson、Bradley L. Nilsson、Sanchita Sarker、Bogdan Doboszewski、Weijian Zhang、Morris J. Robins

  DOI：10.1021/jo9908647

  日期：1999.10.1

  Treatment of tert-butyldimethylsilyl (TBDMS) derivatives of 3'-keto(adenosine or uridine) with [(ethoxycarbonyl)methylene]triphenylphosphorane gave exocyclic alkenes that underwent stereoselective hydrogenation to give 3'-deoxy-3'-[(ethoxycarbonyl)methyl](Ado or Urd) analogues. Saponification provided the 3'-(carboxymethyl)-3'-deoxy(Ado and Urd) derivatives 37 and 38. Treatment of 37 or 38 with DCC and 5'-amino-2',3'-bis-O-TBDMS-5'-deoxynucleosides gave the amide-linked dimers (74-82%). Activation of 37 or 38 with 4-nitrophenol/DCC, and direct coupling of the 4-nitrophenyl esters with 5'-amino-5'-deoxy(Ado or Urd) in pyridine also produced amide dimers efficiently (65-70%). Analogous activation of a 5'-O-DMT-protected carboxylate, and its coupling with 5'-amino-5'-deoxy-2'-O-methyladenosine gave the amide dimer in good yield (74%). Coupling (DCC) of a 5'-azido-2'-O-TBDMS-3'-(carboxymethyl)-3', 5'-dideoxyuridine intermediate with 5'-amino-5'-deoxynucleosides gave amide-linked dimers (72-78%) that can serve as masked (azide reduction) 5'-amino dimers for analogous synthesis of extended amide-linked oligomers.