(2R,3S,5R)-5-[4-amino-3-[6-[1-[2-[2-[4-[6-[4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrazolo[3,4-d]pyrimidin-3-yl]hex-5-ynyl]triazol-1-yl]ethoxy]ethyl]triazol-4-yl]hex-1-ynyl]pyrazolo[3,4-d]pyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-ol | 1257843-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: (2R,3S,5R)-5-[4-amino-3-[6-[1-[2-[2-[4-[6-[4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrazolo[3,4-d]pyrimidin-3-yl]hex-5-ynyl]triazol-1-yl]ethoxy]ethyl]triazol-4-yl]hex-1-ynyl]pyrazolo[3,4-d]pyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 1257843-79-0
• 化学式: C₄₀H₅₀N₁₆O₇
• 分子量: 866.94
• InChiKey: BHDUIMUGARWUGA-XLTUSUNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  63
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  309
• 氢给体数：
  6
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  1-叠氮基-2-(2-叠氮基乙氧基)乙烷 、 1-(2-deoxy-β-D-erythro-pentofuranosyl)-3-(octa-1,7-diynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 12.0h， 以89%的产率得到(2R,3S,5R)-5-[4-amino-3-[6-[1-[2-[2-[4-[6-[4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrazolo[3,4-d]pyrimidin-3-yl]hex-5-ynyl]triazol-1-yl]ethoxy]ethyl]triazol-4-yl]hex-1-ynyl]pyrazolo[3,4-d]pyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-ol
  参考文献：
  名称：

  Cross-Linked DNA Generated by “Bis-click” Reactions with Bis-functional Azides: Site Independent Ligation of Oligonucleotides via Nucleobase Alkynyl Chains

  摘要：

  Template-free cross-linking of single-stranded DNA bearing octadiynyl side chains at the 7-position of 8-aza-7-deazapurine moieties with bisfunctional azides is reported employing a Cu(I)-catalyzed azide alkyne "bis-click" reaction. Bis-adducts were formed when the bis-azide:oligonucleotide ratio was 1:1; monofunctionalization occurred when the ratio was 15:1. Four-stranded DNA consisting of two cross-linked duplexes was obtained after hydridization. Cross-linked duplexes are as stable as individual duplexes when ligation was introduced at terminal positions; ligation at a central position led to a slight duplex destabilization.

  DOI：

  10.1021/jo101809w

文献信息

• Cross-Linked DNA Generated by “Bis-click” Reactions with Bis-functional Azides: Site Independent Ligation of Oligonucleotides via Nucleobase Alkynyl Chains
  作者：Suresh S. Pujari、Hai Xiong、Frank Seela

  DOI：10.1021/jo101809w

  日期：2010.12.17

  Template-free cross-linking of single-stranded DNA bearing octadiynyl side chains at the 7-position of 8-aza-7-deazapurine moieties with bisfunctional azides is reported employing a Cu(I)-catalyzed azide alkyne "bis-click" reaction. Bis-adducts were formed when the bis-azide:oligonucleotide ratio was 1:1; monofunctionalization occurred when the ratio was 15:1. Four-stranded DNA consisting of two cross-linked duplexes was obtained after hydridization. Cross-linked duplexes are as stable as individual duplexes when ligation was introduced at terminal positions; ligation at a central position led to a slight duplex destabilization.