N²-(4,4'-dimethoxytrityl)-2'-deoxyguanosine | 16369-01-0

• 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: N²-(4,4'-dimethoxytrityl)-2'-deoxyguanosine
• 英文别名: 2-[[bis(4-methoxyphenyl)-phenylmethyl]amino]-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 16369-01-0
• 化学式: C₃₁H₃₁N₅O₆
• 分子量: 569.617
• InChiKey: YARWUWMYPWTLDK-JIMJEQGWSA-N

物化性质

• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N²-(4,4'-dimethoxytrityl)-2'-deoxyguanosine 生成 N2-dimethoxytrityl-5'-amino-2',5'-dideoxyguanosine
  参考文献：
  名称：

  含有N-氰基胍键的寡核苷酸的合成，酶稳定性和理化性质。

  摘要：

  合成具有N-氰基胍键的核苷二聚体，并用作寡核苷酸合成的结构单元。由交替的磷酸二酯和氰基胍功能组成的寡核苷酸仍然能够与互补的天然寡脱氧核苷酸杂交。

  DOI：

  10.1016/s0040-4020(01)85246-7
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 吡啶 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 24.58h， 生成 N²-(4,4'-dimethoxytrityl)-2'-deoxyguanosine
  参考文献：
  名称：

  Functionalization of solid supports with N-unprotected deoxyribonucleosides

  摘要：

  N-Unprotected deoxyribonucleotides were loaded to solid supports via a succinyl or an oxalyl linker. These solid supports were successfully used for oligonucleotide synthesis by the H-phosphonate method without N-protecting groups. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01129-0

文献信息

• The Efficiency of Light-Directed Synthesis of DNA Arrays on Glass Substrates
  作者：Glenn H. McGall、Anthony D. Barone、Martin Diggelmann、Stephen P. A. Fodor、Erik Gentalen、Nam Ngo

  DOI：10.1021/ja964427a

  日期：1997.6.1

  New methods based on photolithography and surface fluorescence were used to determine photodeprotection rates and stepwise yields for light-directed oligonucleotide synthesis using photolabile 5‘-(((α-methyl-2-nitropiperonyl)oxy)carbonyl)(MeNPOC)-2‘-deoxynucleoside phosphoramidites on planar glass substrates. Under near-UV illumination (primarily 365 nm) from a mercury light source, the rate of photoremoval

  基于光刻和表面荧光的新方法用于确定使用光不稳定 5'-(((α-methyl-2-nitropiperonyl)oxy)carbonyl)(MeNPOC)-2'-的光导向寡核苷酸合成的光脱保护速率和逐步产率平面玻璃基板上的脱氧核苷亚磷酰胺。在来自汞光源的近紫外线照射（主要是 365 nm）下，发现 MeNPOC 保护基团的光去除率与生长的寡聚体的核苷酸和长度无关（t1/2 = 12 s，27.5 mW /cm2）。观察到对溶剂极性的适度依赖性，在存在非极性溶剂或不存在溶剂的情况下，光解进行得最快（例如，t1/2 = 10-13 s，27.5 mW/cm2）。在解决方案中，光解速率在 5-50 mW/cm2 范围内与光强度呈线性关系。使用基于 N6-(苯氧基乙酰基)-2'-脱氧腺苷的单体合成十二聚体寡核苷酸的平均逐步产率在 92-94% 的范围内。
• Highly chemo- and regioselective phosphitylation of unprotected 2′-deoxyribonucleosides
  作者：Yukiko Kato、Natsuhisa Oka、Takeshi Wada

  DOI：10.1016/j.tetlet.2006.02.060

  日期：2006.4

  regioselective phosphitylation of unprotected 2′-deoxyribonucleosides by the use of di-tert-butyl N,N-diethylphosphoramidite, a sterically hindered phosphoramidite. Both N/O- and primary hydroxy group-selectivities were simultaneously achieved, and the selectivity for the 5′-hydroxy groups was up to 97% regardless of the base moiety of the 2′-deoxyribonucleosides. The 3′-O-isomers and the 5′-O-isomers were easily

  我们已经通过使用二叔丁基N，N-二乙基亚磷酰胺，一种位阻的亚磷酰胺，开发了未保护的2'-脱氧核糖核苷的化学和区域选择性磷酸化。同时实现N / O-和伯羟基选择性，并且无论2'-脱氧核糖核苷的碱基部分如何，对5'-羟基的选择性均高达97％。通过硅胶柱色谱法或结晶容易地分离3'-O-异构体和5'-O-异构体，以中等至良好的产率得到纯的2'-脱氧核糖核苷5'-亚磷酸酯。
• Functionalization of solid supports with N-unprotected deoxyribonucleosides
  作者：Takeshi Wada、Akira Mochizuki、Yuichi Sato、Mitsuo Sekine

  DOI：10.1016/s0040-4039(98)01129-0

  日期：1998.7

  N-Unprotected deoxyribonucleotides were loaded to solid supports via a succinyl or an oxalyl linker. These solid supports were successfully used for oligonucleotide synthesis by the H-phosphonate method without N-protecting groups. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis, enzymatic stability and physicochemical properties of oligonucleotides containing a N-cyanoguanidine linkage.
  作者：C. Pannecouque、F. Vandendriessche、J. Rozenski、G. Janssen、R. Busson、A. Van Aerschot、P. Claes、P. Herdewijn

  DOI：10.1016/s0040-4020(01)85246-7

  日期：1994.1

  Nucleoside dimers with a N-cyanoguanidine linkage were synthesized and used as building blocks for oligonucleotide synthesis. Oligonucleotides composed of alternating phosphodiester and cyanoguanidine functions are still able to hybridize with a complementary natural oligodeoxynucleotide.

  合成具有N-氰基胍键的核苷二聚体，并用作寡核苷酸合成的结构单元。由交替的磷酸二酯和氰基胍功能组成的寡核苷酸仍然能够与互补的天然寡脱氧核苷酸杂交。