5'-O-dabsylthymidine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-dabsylthymidine
• 化学式: C₂₄H₂₇N₅O₇S
• 分子量: 529.574
• InChiKey: UIHSSCIBLAXVJG-INODYBPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  155.65
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5'-O-dabsylthymidine 、 bis(diisopropylamino)(2-cyanoethoxy)phosphane 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到5'-O-dabsylthymidine cyanoethyl-N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Quencher as Leaving Group:  Efficient Detection of DNA-Joining Reactions

  摘要：

  We describe a new fluorescence reporting strategy in which dabsyl, a well-known quencher, activates a hydroxyl group in a probe to convert it to a leaving group. When a nucleophilic phosphorothioate probe binds adjacent to a dabsyl quenched probe, autoligation occurs, releasing the quencher, and lighting up the probes, This signal change can be used to detect single nucleotide differences in DNA without enzymes or reagents.

  DOI：

  10.1021/ja017328s
• 作为产物：
  描述：

  (E)-4-((4-(dimethylamino)phenyl)diazenyl)benzene-1-sulfonyl chloride 、 beta-胸苷 以 吡啶 为溶剂， 反应 24.0h， 以44%的产率得到5'-O-dabsylthymidine
  参考文献：
  名称：

  Quencher as Leaving Group:  Efficient Detection of DNA-Joining Reactions

  摘要：

  We describe a new fluorescence reporting strategy in which dabsyl, a well-known quencher, activates a hydroxyl group in a probe to convert it to a leaving group. When a nucleophilic phosphorothioate probe binds adjacent to a dabsyl quenched probe, autoligation occurs, releasing the quencher, and lighting up the probes, This signal change can be used to detect single nucleotide differences in DNA without enzymes or reagents.

  DOI：

  10.1021/ja017328s

文献信息

• DETECTION OF CHEMICAL LIGATION USING FLUORESCENCE QUENCHING LEAVING GROUPS
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：EP1543156A2

  公开（公告）日：2005-06-22
• EP1543156A4
  申请人：——

  公开号：EP1543156A4

  公开（公告）日：2005-12-21
• US7749699B2
  申请人：——

  公开号：US7749699B2

  公开（公告）日：2010-07-06
• [EN] DETECTION OF CHEMICAL LIGATION USING FLUORESCENCE QUENCHING LEAVING GROUPS<br/>[FR] DETECTION DE LIGATURES CHIMIQUES A L'AIDE DE GROUPES PARTANTS D'EXTINCTION DE FLUORESCENCE
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2004010101A2

  公开（公告）日：2004-01-29

  Novel compounds having a fluorescence quencher as a leaving group are disclosed. Nucleic acids and other molecules containing a fluorophore and a fluorescence quencher are disclosed as an embodiment of this invention. The use of the oligonucleotides in enzyme-free oligonucleotide ligation reactions results in an increase in fluorescence when the oligonucleotide also contains a nearby fluorophore. The ligation reactions can be performed in solution, on surfaces, or in cells.
• Quencher as Leaving Group:  Efficient Detection of DNA-Joining Reactions
  作者：Shinsuke Sando、Eric T. Kool

  DOI：10.1021/ja017328s

  日期：2002.3.1

  We describe a new fluorescence reporting strategy in which dabsyl, a well-known quencher, activates a hydroxyl group in a probe to convert it to a leaving group. When a nucleophilic phosphorothioate probe binds adjacent to a dabsyl quenched probe, autoligation occurs, releasing the quencher, and lighting up the probes, This signal change can be used to detect single nucleotide differences in DNA without enzymes or reagents.