O^5'-(4,4'-dimethoxy-trityl)-2'-deoxy-[3']adenylic acid | 106713-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: O^5'-(4,4'-dimethoxy-trityl)-2'-deoxy-[3']adenylic acid
• 英文别名: DMT(-5)2-deoxy-D-eryPenf3P(b)-adenin-9-yl；[(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl] dihydrogen phosphate
• CAS: 106713-36-4
• 化学式: C₃₁H₃₂N₅O₈P
• 分子量: 633.598
• InChiKey: SJRMSNQQZDFEPC-OYUWMTPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  173
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  O^5'-(4,4'-dimethoxy-trityl)-2'-deoxy-[3']adenylic acid 在 二氯乙酸 作用下， 生成 2' -脱氧3' -磷酸游离酸
  参考文献：
  名称：

  A Facile Method for the Oxidation of Nucleoside H-Phosphonates to Phosphates with Bis(trimethylsilyl) Peroxide

  摘要：

  我们开发了一种便捷的方法，在催化剂三甲基硅基三氟甲磺酸酯的作用下，用双（三甲基硅基）过氧化物和N，O-双（三甲基硅基）乙酰胺实现核苷H-膦酸单酯和二酯的氧化。

  DOI：

  10.1055/s-1999-2951
• 作为产物：
  描述：

  1,8-diazabicyclo[5.4.0]undec-7-enium 5'-O-(4,4'-dimethoxytrityl)deoxyadenosin-3'-yl phosphonate 在 双(三甲基硅基)过氧化物 、 三氟甲磺酸三甲基硅酯 、 N,O-bis(trimethylsilyl)benzamide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以97%的产率得到O^5'-(4,4'-dimethoxy-trityl)-2'-deoxy-[3']adenylic acid
  参考文献：
  名称：

  A Facile Method for the Oxidation of Nucleoside H-Phosphonates to Phosphates with Bis(trimethylsilyl) Peroxide

  摘要：

  我们开发了一种便捷的方法，在催化剂三甲基硅基三氟甲磺酸酯的作用下，用双（三甲基硅基）过氧化物和N，O-双（三甲基硅基）乙酰胺实现核苷H-膦酸单酯和二酯的氧化。

  DOI：

  10.1055/s-1999-2951

文献信息

• New Nucleoside-Based Polymeric Supports for the Solid Phase Synthesis of Ribose-Modified Nucleoside Analogues
  作者：Giovanni Di Fabio、Lorenzo De Napoli、Jennifer D’Onofrio、Daniela Montesarchio

  DOI：10.1055/s-2004-830864

  日期：——

  New solid supports, linking protected pyrimidine and purine nucleoside derivatives through the nucleobase, have been prepared. The support, incorporating a suitable derivative of 2'-azido, 2'-deoxyuridine, allowed the simple and efficient solid-phase synthesis of ribose-modified nucleoside and nucleic acid analogues, particularly of aminoacyl derivatives of 2'-deoxy, 2'-amino-uridine, following methodologies

  已经制备了新的固体支持物，通过核碱基连接受保护的嘧啶和嘌呤核苷衍生物。包含合适的 2'-叠氮基、2'-脱氧尿苷衍生物的载体允许简单有效地固相合成核糖修饰的核苷和核酸类似物，特别是 2'-脱氧、2'-氨基酰基衍生物氨基尿苷，遵循肽和寡核苷酸化学中成熟的方法。
• Use of a thiol tether for the site-specific attachment of reporter groups to DNA
  作者：Jacqueline A. Fidanza、Larry W. McLaughlin

  DOI：10.1021/jo00034a028

  日期：1992.4

  The sequence-specific incorporation of a thiol tether into oligodeoxynucleotides provides for the rapid and facile attachment of a wide variety of reporter groups employing thiol-specific alkylating functionalities. The thiol residue is introduced into the DNA by oxidation of an internucleotide H-phosphonate at a unique site within the sequence in the presence of cystamine. After synthesis and purification of the cystamine-containing oligodeoxynucleotide, the sulfhydryl residue is unmasked by a short treatment with dithiothreitol. The tethered sulfhydryl residue is amenable to modification by a variety of thiol-specific reporter groups. Nuclease digests of the modified and unmodified sequences confirm that labeling occurs at the site of the tether. Duplex sequences containing a variety of fluorophores covalently bound through this thiol tether exhibit thermal stabilities that are very similar to that of the unlabeled sequence.
• Hayakawa, Yoshihiro; Kawai, Rie; Wakabayashi, Shigeharu, Nucleosides and Nucleotides, 1998, vol. 17, # 1-3, p. 441 - 449
  作者：Hayakawa, Yoshihiro、Kawai, Rie、Wakabayashi, Shigeharu、Uchiyama, Mamoru、Noyori, Ryoji

  DOI：——

  日期：——