2'-deoxy-3',5'-bis-O-(triisopropylsilyl)guanosine | 109460-89-1

• 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: 2'-deoxy-3',5'-bis-O-(triisopropylsilyl)guanosine
• 英文别名: 3',5'-O-Bis(triisopropylsilyl)-2'-deoxyguanosine；3',5'-di-O-(triisopropylsilyl)-2'-deoxyguanosine；2'-Deoxy-3',5'-bis(triisopropylsilyl)guanosine；2'-deoxy-3',5'-di-O-triisopropylsilylguanosine；2'-deoxy-3',5'-di(triisopropylsilyl)guanosine；3',5'-di-triisopropylsilyl-2'-deoxyguanasine；2-amino-9-[(2R,4S,5R)-4-tri(propan-2-yl)silyloxy-5-[tri(propan-2-yl)silyloxymethyl]oxolan-2-yl]-1H-purin-6-one
• CAS: 109460-89-1
• 化学式: C₂₈H₅₃N₅O₄Si₂
• 分子量: 579.931
• InChiKey: MYROMHRTRYYNHH-RBZQAINGSA-N

物化性质

• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.74
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-deoxy-3',5'-bis-O-(triisopropylsilyl)guanosine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以38%的产率得到8-溴-2'-脱氧鸟苷
  参考文献：
  名称：

  An Improved Synthesis of 8-Bromo-2′-deoxyguanosine

  摘要：

  A new synthesis of 8-bromo-2-deoxyguanosine, a key intermediate in the synthesis of the mutagenic DNA adduct 8-oxo-2'-deoxyguanosine is described. The advantages of this method are significantly improved yields and ease of isolation.

  DOI：

  10.1080/00397919308011257
• 作为产物：
  描述：

  三异丙基氯硅烷 、 2'-脱氧鸟苷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以61%的产率得到2'-deoxy-3',5'-bis-O-(triisopropylsilyl)guanosine
  参考文献：
  名称：

  新型鸟苷二位受体的合成与表征

  摘要：

  已经制备并表征了鸟苷的新型二位受体。它们与亲脂性鸟苷衍生物的缔合常数略小于鸟苷-胞苷碱基对的预期值，但仍在构建超分子结构的有用范围内。

  DOI：

  10.1016/s0040-4020(03)00708-7

文献信息

• Boron-containing nucleic acids. Synthesis of cyanoborane adducts of 2'-deoxynucleosides
  作者：Anup Sood、Barbara Ramsay Shaw、Bernard F. Spielvogel

  DOI：10.1021/ja00208a019

  日期：1989.12

  Cyanoborane adducts of 2'-deoxynucleosides, specifically 2'-deoxyguanosine-N7-cyanoborane, 2'-deoxyadenosine-N1-cyanoborane, 2'-deoxyinosine-N7-cyanoborane, and 2'-deoxycytidine-N3-cyanoborane, were prepared by an exchange reaction of triphenylphosphine-cyanoborane (Ph 3 PBH 2 CH) with 3',5'-O-protected nucleosides

  2'-脱氧核苷的氰硼烷加合物，特别是 2'-脱氧鸟苷-N7-氰基硼烷、2'-脱氧腺苷-N1-氰基硼烷、2'-脱氧肌苷-N7-氰基硼烷和 2'-脱氧胞苷-N3-氰基硼烷，由三苯基膦-氰基硼烷 (Ph 3 PBH 2 CH) 与 3',5'-O-保护的核苷的交换反应
• Sood; Shaw; Spielvogel, Pharmazie, 1992, vol. 47, # 11, p. 833 - 838
  作者：Sood、Shaw、Spielvogel、Hall、Chi、Hall

  DOI：——

  日期：——
• Vibrational analysis of the hydrogen bonding of cytidine and guanosine derivatives
  作者：Pedro Carmona、Marina Molina、Aurora Lasagabaster、Rosario Escobar、Aida Ben Altabef

  DOI：10.1021/j100139a042

  日期：1993.9

  Hydrogen bonding between 2'-deoxy-3',5'-bis(triisopropylsilyl)guanosine (G) and 2'-deoxy-3',5'-bis(triisopropylsilyl) cytidine (C) has been studied by vibrational spectroscopy in chloroform solution. Strong interactions occur between the two derivatives of guanosine and cytidine and between CG base pair and cytidine, whose association constants were first determined. CGC trimers involve cyclic hydrogen bonds through the N(3) acceptors of both nucleobases and the guanine N(2)H and cytosine N(4)H donors. The main spectral changes of CG dimer accompanying CGC trimer formation are intensity and frequency decreases of the Raman band of guanine base near 1570 cm-1 as well as downshifting of the 1534-cm-1 Raman band of the cytosine base that binds to the previously formed CG base pair. Similar spectral changes are observed for the infrared bands located near these frequencies. The 1483-cm-1 band of guanine is sensitive to hydrogen bonding at the N(7) position. Since this band is unchanged when the CG dimer is converted to the CGC trimer, it is concluded that no binding at the G(7) position occurs in the trimer. Raman spectroscopy can, then, distinguish between hydrogen bonds involving guanine N(7) and N(3) acceptors and offers prospect for determining these specific interactions in polynucleotide triplexes and nucleic acid-protein recognition.
• Synthesis and characterisation of new ditopic receptors for guanosine
  作者：Andrew Marsh、Nathaniel W Alcock、William Errington、Rajeeve Sagar

  DOI：10.1016/s0040-4020(03)00708-7

  日期：2003.7

  Novel ditopic receptors for guanosine have been prepared and characterised. Their association constants with a lipophilic guanosine derivative are somewhat smaller than the expected values for a guanosine–cytidine base pair, but remain in a useful range for building supramolecular structures.

  已经制备并表征了鸟苷的新型二位受体。它们与亲脂性鸟苷衍生物的缔合常数略小于鸟苷-胞苷碱基对的预期值，但仍在构建超分子结构的有用范围内。
• An Improved Synthesis of 8-Bromo-2′-deoxyguanosine
  作者：Peter M. Gannett、Tushar P. Sura

  DOI：10.1080/00397919308011257

  日期：1993.6

  A new synthesis of 8-bromo-2-deoxyguanosine, a key intermediate in the synthesis of the mutagenic DNA adduct 8-oxo-2'-deoxyguanosine is described. The advantages of this method are significantly improved yields and ease of isolation.