2-氨基-3,7-二氢-5-碘-7-[(2R,5S)-四氢-5-(羟基甲基)-2-呋喃基]-4H-吡咯并[2,3-D]嘧啶-4-酮 | 114748-67-3

• 物质功能分类: 生物化工 - 生化试剂
• 分子结构分类: 有机化合物
• 中文名称: 2-氨基-3,7-二氢-5-碘-7-[(2R,5S)-四氢-5-(羟基甲基)-2-呋喃基]-4H-吡咯并[2,3-D]嘧啶-4-酮
• 英文名称: 7-iodo-2',3'-dideoxy-7-deazaguanosine
• 英文别名: 7-Iodo-2',3'-Dideoxy-7-Deaza-Guanosine；2-amino-7-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-3H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS: 114748-67-3
• 化学式: C₁₁H₁₃IN₄O₃
• 分子量: 376.154
• InChiKey: KJNOBXXCZQLWLF-CAHLUQPWSA-N

物化性质

• 密度：
  2.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

生物活性

7-Iodo-2',3'-dideoxy-7-deazaadenosine 是一种双脱氧核苷，可用于 DNA 合成和测序反应。

反应信息

• 作为反应物：
  描述：

  2-氨基-3,7-二氢-5-碘-7-[(2R,5S)-四氢-5-(羟基甲基)-2-呋喃基]-4H-吡咯并[2,3-D]嘧啶-4-酮 在 copper(l) iodide 、 四(三苯基膦)钯 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 7-Deaza-7-propargylamino-ddGTP
  参考文献：
  名称：

  Confalone, Pat. N., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 1, p. 31 - 46

  摘要：

  DOI：
• 作为产物：
  描述：

  5-iodo-2-methylsulfanyl-7-[(2R,5S)-5-(trityloxymethyl)oxolan-2-yl]-1H-pyrrolo[2,3-d]pyrimidin-4-one 在 甲酸 、 氨 、 3-氯苯甲酸 作用下， 反应 3.17h， 生成 2-氨基-3,7-二氢-5-碘-7-[(2R,5S)-四氢-5-(羟基甲基)-2-呋喃基]-4H-吡咯并[2,3-D]嘧啶-4-酮
  参考文献：
  名称：

  7-碘-2'，3'-二脱氧-7-脱氮嘌呤核苷的全合成，这是制备用于DNA自动测序的试剂的关键中间体

  摘要：

  描述了7-碘-2'，3'-二脱氧-7-脱氮杂腺苷和7-碘-2'，3'-二脱氧-7-脱氮鸟苷的实用合成。这些碘核苷可以转化为DNA聚合酶的荧光标记的链终止底物。

  DOI：

  10.1016/s0040-4039(00)80417-7

文献信息

• Solvent, not palladium oxidation state, is the primary determinant for successful coupling of terminal alkynes with iodo-nucleosides
  作者：Morris J. Robins、Ravi S. Vinayak、Steven G. Wood

  DOI：10.1016/s0040-4039(00)97456-2

  日期：——

  Coupling of iodo-nucleosides with terminal alkynes such as 3-(acylamino)propynes, whose initial products readily undergo secondary cyclization reactions, can be effected smoothly by the standard catalysis with (Ph3P)2PdCl2/CuI/Et3N in dimethylformamide.

  碘代核苷与末端炔烃（例如3-（酰基氨基）丙炔）的偶联，其初始产物容易发生二级环化反应，可以通过（Ph 3 P）2 PdCl 2 / CuI / Et 3 N in二甲基甲酰胺。
• COCUZZA, ANTHONY J., TETRAHEDRON LETT., 29,(1988) N 33, C. 4061-4064
  作者：COCUZZA, ANTHONY J.

  DOI：——

  日期：——
• Method for Detecting Target Nucleic Acid with Specific Base Sequence and Set of Nucleic Acids for Detection
  申请人：Fujimoto Kenzo

  公开号：US20090221429A1

  公开（公告）日：2009-09-03

  It is intended to provide a method for detecting a target nucleic acid with a specific base sequence existing in a sample mixture with high specificity and sensitivity by utilizing the formation of a hybrid with a complementary strand as a detection principle, and a nucleic acid for the detection. The invention relates to a set of nucleic acids for detecting a target nucleic acid with a specific base sequence comprising a photoligating nucleic acid composed of a nucleic acid (with the proviso that in the nucleic acid, a nucleic acid and a peptide nucleic acid are included) having a group represented by the formula I, II, III, IV or V described in claims at the 5′ end or 3′ end as a base moiety, and a photoligated nucleic acid having a base with a carbon-carbon double bond at the 3′ end or 5′ end as a base moiety capable of photoligating to the photoligating nucleic acid, wherein either of the photoligating nucleic acid and the photoligated nucleic acid has a labeling moiety and the other remaining nucleic acid is immobilized on a substrate, and the method for detecting a target nucleic acid with a specific base sequence by using the set of nucleic acids.
• US7851159B2
  申请人：——

  公开号：US7851159B2

  公开（公告）日：2010-12-14