N²-isobutyryl-2'-deoxyguanosine | 190834-08-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N²-isobutyryl-2'-deoxyguanosine
• 英文别名: N⁶-isobutyryl-2'-deoxyadenosine；N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]-2-methylpropanamide
• CAS: 190834-08-3
• 化学式: C₁₄H₁₉N₅O₄
• 分子量: 321.336
• InChiKey: GHMARNHYJYPWRH-IVZWLZJFSA-N

物化性质

• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N²-isobutyryl-2'-deoxyguanosine 在 ammonium hydroxide 作用下， 反应 3.0h， 生成 2'-脱氧腺苷
  参考文献：
  名称：

  Synthesis of oligonucleotides containing 3'-alkyl amines using N-isobutyryl protected deoxyadenosine phosphoramidite

  摘要：

  Oligonucleotides were synthesized using the N-isobutyryldeoxyadenosine protected beta-cyanoethyl phosphoramidite, 9. The oligonucleotides that were synthesized using 9 can be deprotected using concentrated NH4OH at 55 degrees C in 2 h. No depurination was detected via anion exchange HPLC. The isobutyryl protected deoxyadenosine did not undergo transamidation with nucleobase and phosphate protected oligonucleotides containing primary alkyl amines, and will be useful in the synthesis of bioconjugates using protected biopolymers. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00568-6
• 作为产物：
  描述：

  9-((2R,4S,5R)-4-Trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamine 在 ammonium hydroxide 作用下， 生成 N²-isobutyryl-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis of oligonucleotides containing 3'-alkyl amines using N-isobutyryl protected deoxyadenosine phosphoramidite

  摘要：

  Oligonucleotides were synthesized using the N-isobutyryldeoxyadenosine protected beta-cyanoethyl phosphoramidite, 9. The oligonucleotides that were synthesized using 9 can be deprotected using concentrated NH4OH at 55 degrees C in 2 h. No depurination was detected via anion exchange HPLC. The isobutyryl protected deoxyadenosine did not undergo transamidation with nucleobase and phosphate protected oligonucleotides containing primary alkyl amines, and will be useful in the synthesis of bioconjugates using protected biopolymers. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00568-6

文献信息

• A new and convenient approach for the preparation of β-cyanoethyl protected trinucleotide phosphoramidites
  作者：Matthäus Janczyk、Bettina Appel、Danilo Springstubbe、Hans-Joachim Fritz、Sabine Müller

  DOI：10.1039/c2ob06934b

  日期：——

  Herein we report a convenient approach for the preparation of fully protected trinucleotide synthons to be used for the synthesis of gene libraries. The trinucleotide synthons bear β-cyanoethyl groups at the phosphate residues, and thus can be used in standard oligonucleotide synthesis without additional steps for deprotection and work-up.

  我们在此报道一种简便的方法，用于制备全保护的三核苷酸合成子，这些合成子将用于基因库的合成。这些三核苷酸合成子在磷酸残基上具有β-氰乙基团，因此可以在标准的寡核苷酸合成中使用，无需额外的去保护和后处理步骤。
• Rapid and Selective Reduction of Amide Group by Borane-Amine Complexes in Acyl Protected Nucleosides
  作者：Zinaida A. Sergueeva、Dmitri S. Sergueev、Barbara Ramsay Shaw

  DOI：10.1080/15257770008033009

  日期：2000.1

  fast and selective reduction of a deoxynucleoside N-acyl group to a corresponding N-alkyl group. Three different nucleosides (dG, dA, and dC) each having one of three N-protecting groups (benzoyl, isobutyryl, or acetyl) were used to prepare N-alkylated nucleosides in good yields under mild conditions. Deoxyribose O-acyl protecting groups remain intact at the conditions of N-acyl group reduction.

  硼烷-胺络合物提供了脱氧核苷N-酰基异常快速且选择性的还原为相应的N-烷基。具有三个N-保护基团（苯甲酰基，异丁酰基或乙酰基）之一的三种不同的核苷（dG，dA和dC）用于在温和条件下以高收率制备N-烷基化的核苷。在N-酰基还原的条件下，脱氧核糖O-酰基保护基保持完整。
• Polymer supported carbodiimide strategy for the synthesis of N-acylated derivatives of deoxy- and ribo purinenucleosides using active esters
  作者：Snehlata Tripathi、Krishna Misra、Yogesh S. Sanghvi

  DOI：10.1016/j.bmcl.2005.07.078

  日期：2005.11

  A cost-effective synthetic strategy has been used for the selective protection of the exocyclic amino function of purine nucleosides. Instead of using the common protecting groups in their chloride or anhydride forms, the less expensive and nontoxic acidic form was chosen. The acids were first activated to an active ester form using DCC and further successfully used for N-acylation of purine nucleosides. The contamination of the N-acylated product with DCU was inconvenient and was avoided by use of polymer supported-carbodiimide that has the additional advantage of reusability. (c) 2005 Elsevier Ltd. All rights reserved.