5'-azido-2',5'-dideoxy-N⁴-benzoylcytidine | 74597-69-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 5'-azido-2',5'-dideoxy-N⁴-benzoylcytidine
• 英文别名: 5'-azido-N⁴-benzoyl-2',5'-dideoxycytidine；5'-azido-N4-benzoyl-2',5'-dideoxycytidine；5'-azido-N⁴-benzoyl-2',5'-dideoxy-cytidine；5'-Azido-N-benzoyl-2',5'-dideoxycytidine；N-[1-[(2R,4S,5R)-5-(azidomethyl)-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 74597-69-6
• 化学式: C₁₆H₁₆N₆O₄
• 分子量: 356.341
• InChiKey: OBDFXIWMWWPQSJ-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-azido-2',5'-dideoxy-N⁴-benzoylcytidine 在 palladium on activated charcoal 吡啶 、 氢气 、 三乙胺 作用下， 以 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 p-nitrophenyl N⁴-benzoyl-2',5'-dideoxy-5'-(4''-monomethoxytrityl)aminocytidine 3'-carbonate
  参考文献：
  名称：

  Uncharged stereoregular nucleic acid analogs. 1. Synthesis of a cytosine-containing oligomer with carbamate internucleoside linkages

  摘要：

  DOI：

  10.1021/jo00228a010
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 在 吡啶 、 三甲基氯硅烷 、 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5'-azido-2',5'-dideoxy-N⁴-benzoylcytidine
  参考文献：
  名称：

  DNG cytidine: synthesis and binding properties of octameric guanidinium-linked deoxycytidine oligomer

  摘要：

  The synthesis of guanidinium-linked cytidyl oligomer (DNG-C-8), a cationic DNA analog, and the corresponding cytidine monomers is described. The DNG monomer synthesis was streamlined to produce a shorter route to the final monomer than previously reported for thymidine and subsequent solid-phase synthesis produced an octameric cytidyl DNG strand. Because octameric deoxyguanosine would be used as the complementary strand in our studies, it was necessary to investigate guanosine self-association. Singular value decomposition was used to mathematically deconvolve the spectral data and confirm the presence of transitions due to DNA-G(8) self-association. Job plots show the binding stoichiometry of DNG-C-8 with DNA-G(8) to be 1: 1. Thermal denaturation studies of the DNG-C-8-DNA-G(8) duplex established a T-m greater than or equal to 90degreesC and a DeltaGdegrees = 13.3 kcal mol(-1), indicating the DNG-C(8)(.)DNA-G(8) duplex is over 1000 times more stable than that of DNA-C(8)(.)DNA-G(8). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.010

文献信息

• Template-Directed Synthesis in 3′- and 5′-Direction with Reversible Termination
  作者：Andreas Kaiser、Sebastian Spies、Tanja Lommel、Clemens Richert

  DOI：10.1002/anie.201203859

  日期：2012.8.13

  Extending both ways: A method for DNA‐templated synthesis on solid support is described. Controlled, stepwise chain extension was demonstrated both in the direction favored by nature (3′‐extension; see scheme) and in the direction typical for conventional DNA synthesizers (5′‐extension).

  两种方法都可以扩展：描述了一种在固相支持物上进行DNA模板合成的方法。在自然界偏爱的方向（3'-延伸；参见方案）和常规DNA合成仪的典型方向（5'-延伸）中都证明了可控的，逐步的链延伸。
• Synthesis of dinucleotides containing a bridged non-chiral internucleotide 5′- or 3′-phosphoramidate linkage
  作者：Matthias Mag、Joachim W. Engels

  DOI：10.1016/s0040-4020(01)81755-5

  日期：1994.8

  The synthesis of several dinucleoside phosphate derivatives which are linked by phosphoramidate bonds [3′-O-P(O)(O−)-NH-5′ or 3′-NH-P(O)(O−)-O-5′] has been accomplished. The internucleoside phosphoramidate linkage was performed using the Staudinger reaction which is directly followed by a Michaelis-Arbuzov type transformation. Due to the exclusive use of base labile blocking groups deprotection could

  通过氨基磷酸酯键[ 3'- O - P（= O）（O -）- NH -5'或3'- NH - P（= O）（O -）- O连接的几种二核苷磷酸酯衍生物的合成-5′]已经完成。使用Staudinger反应进行核苷间氨基磷酸酯键合，然后直接进行Michaelis-Arbuzov型转化。由于仅使用碱不稳定的封闭基团，因此可以非常简单地通过在55°C下用浓氨水处理24小时来轻松进行脱保护。
• 5′-modified nucleotides and the application thereof in molecular biology and medicine
  申请人：Europaisches Laboratorium fur Molekularbiologie (EMBL)

  公开号：US06627416B1

  公开（公告）日：2003-09-30

  The invention relates to 5′-modified nucleotides and to nucleic acids which contain these nucleotides. Processes for incorporating the 5′-modified nucleotides into nucleic acids, and the subsequent site-specific cleavage of the nucleic acids at the 5′-modified monomer building blocks, are also disclosed. These processes can be employed for nucleic acid sequencing, for generating nucleic acid libraries, for detecting mutations, for preparing support-bound nucleic acids and for pharmaceutical purposes.

  这项发明涉及5'-修饰核苷酸以及含有这些核苷酸的核酸。揭示了将5'-修饰核苷酸并入核酸中的过程，以及在5'-修饰单体构建块处对核酸进行后续的特异性切割。这些过程可用于核酸测序、生成核酸文库、检测突变、制备支持结合的核酸以及药物用途。
• Yamamoto, Isamu; Sekine, Mitsuo; Hata, Tsujiaki, Journal of the Chemical Society. Perkin transactions I, 1980, p. 306 - 310
  作者：Yamamoto, Isamu、Sekine, Mitsuo、Hata, Tsujiaki

  DOI：——

  日期：——
• SPROAT, BRIAN S.;BEIJER, BARBRO;RIDER, PETER, NUCL. ACIDS RES., 15,(1987) N 15, 6181-6196
  作者：SPROAT, BRIAN S.、BEIJER, BARBRO、RIDER, PETER

  DOI：——

  日期：——