5'-N-monomethoxytrityl-3'-amino-3',5'-dideoxythymidine | 209255-51-6

• 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: 5'-N-monomethoxytrityl-3'-amino-3',5'-dideoxythymidine
• 英文别名: 5'-monomethoxytritylamino-3'-amino-2',3',5'-trideoxythymidine；1-[(2R,4S,5R)-4-amino-5-[[[(4-methoxyphenyl)-diphenylmethyl]amino]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 209255-51-6
• 化学式: C₃₀H₃₂N₄O₄
• 分子量: 512.608
• InChiKey: PENLCZRHWABDFC-OYUWMTPXSA-N

物化性质

• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-N-monomethoxytrityl-3'-amino-3',5'-dideoxythymidine 在 TEA 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 3.25h， 生成 [[(2R,3S,5R)-2-({[(4-Methoxy-phenyl)-diphenyl-methyl]-amino}-methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-(2,2,2-trifluoro-acetyl)-amino]-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis of DNA analogues with novel carboxamidomethyl phosphonamide and glycinamide internucleoside linkages

  摘要：

  Thymidine oligonucleotide analogues with phosphodiester bonds fully substituted by carboxamidomethyl phosphonamide, or glycinamide linkages were synthesized on a solid support, and their hybridization properties toward DNA and RNA targets were determined by Tm analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00153-x
• 作为产物：
  描述：

  5-氨基-5-脱氧胸腺嘧啶脱氧核苷 在 吡啶 、 4-二甲氨基吡啶 、 叠氮化锂 、 硫化氢 、 potassium phtalimide 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5'-N-monomethoxytrityl-3'-amino-3',5'-dideoxythymidine
  参考文献：
  名称：

  Solid-phase synthesis of oligomeric deoxynucleic-thiourea (DNT) and deoxynucleic S -methylthiourea (DNmt): a neutral/polycationic analogue of DNA

  摘要：

  A solid-phase synthesis for oligomeric DNmt is reported. Synthesis proceeds in 3'-5' direction and involves coupling of a protected 3'-isothiocyanate with the corresponding 5'-amine of the growing oligo chain. The difference in oligomeric thiourea/ S-methylthiourea binding to DNA is investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00085-8

文献信息

• Solid-Phase Synthesis of Positively Charged Deoxynucleic Guanidine (DNG) Tethering a Hoechst 33258 Analogue:  Triplex and Duplex Stabilization by Simultaneous Minor Groove Binding
  作者：Putta Mallikarjuna Reddy、Thomas C. Bruice

  DOI：10.1021/ja031557s

  日期：2004.3.1

  charged guanidine replaces the phosphodiester linkages, tethering to Hoechst 33258 fluorophore by varying lengths has been synthesized. A pentameric thymidine DNG was synthesized on solid phase in the 3' --> 5' direction that allowed stepwise incorporation of straight chain amino acid linkers and a bis-benzimidazole (Hoechst 33258) ligand at the 5'-terminus using PyBOP/HOBt chemistry. The stability

  脱氧核胍 (DNG) 是一种 DNA 类似物，其中带正电荷的胍取代了磷酸二酯键，通过不同长度与 Hoechst 33258 荧光团相连。在固相上以 3' --> 5' 方向合成了五聚体胸苷 DNG，允许使用 PyBOP/HOBt 化学在 5'-末端逐步掺入直链氨基酸接头和双苯并咪唑 (Hoechst 33258) 配体. (DNA)(2).DNG-H 三链体和 DNA.DNG-H 双链体的稳定性由 DNG 和 DNG-Hoechst 33258 (DNG-H) 偶联物​​与 30 聚体双链 (ds) DNA、d(CGCCGCGCGCGCGAAAAACCCGGCGCGCGC) 形成)/d(GCGGCGCGCGCGCTTTTTGGGCCGCGCGCG) 和单链 (ss) DNA，5'-CGCCGCGCGCGCGAAAAACCCGGCGCGCGC-3'，分别通过热熔解和荧光发射实验进行了评估。在
• Mercury-Free Automated Synthesis of Guanidinium Backbone Oligonucleotides
  作者：Kacper Skakuj、Katherine E. Bujold、Chad A. Mirkin

  DOI：10.1021/jacs.9b09937

  日期：2019.12.26

  of 95% and has enabled the synthesis of a 20-mer DNG oligonucleotide, the longest DNG strand to date, in addition to mixed DNA-DNG sequences with 3-9 DNG inserts. Importantly, DNG oligonucleotides exhibit robust unaided cellular uptake as compared to unmodified oligonucleotides without apparent cellular toxicity. Taken together, these findings should greatly increase the accessibility of cationic backbone

  报道了一种使用碘作为温和且廉价的偶联剂合成脱氧核胍 (DNG) 寡核苷酸的新方法。这种方法不需要以往用于制备 DNG 寡核苷酸的方法中使用的有毒汞盐和刺激性苯硫酚。这种偶联策略很容易转化为标准的 MerMade 12 寡核苷酸合成仪，偶联率为 95%，并且能够合成 20 mer DNG 寡核苷酸，这是迄今为止最长的 DNG 链，以及混合 DNA-DNG 序列与 3- 9 个 DNG 插件。重要的是，与没有明显细胞毒性的未修饰寡核苷酸相比，DNG 寡核苷酸表现出强大的独立细胞摄取。综合起来，
• Deoxynucleic Guanidines (DNG)- Modified Oligonucleotides and Methods of Synthesizing Deoxynucleic Guanidine Strands
  申请人：NORTHWESTERN UNIVERSITY

  公开号：US20200399304A1

  公开（公告）日：2020-12-24

  Disclosed herein are spherical nucleic acids (SNAs) comprising oligonucleotides comprising one or more modified oligonucleotides, and methods of use thereof. Also disclosed are methods of synthesizing modified oligonucleotides for use in therapeutics, including deoxynucleic guanidine (DNG)-modified oligonucleotides.

  本文披露了包含寡核苷酸的球形核酸（SNAs），其中寡核苷酸包括一个或多个修饰的寡核苷酸，并且其使用方法。还披露了用于合成用于治疗的修饰寡核苷酸的方法，包括脱氧核酸胍（DNG）修饰的寡核苷酸。
• Solid-Phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide mixed sequences
  作者：Putta Mallikarjuna Reddy、Thomas C. Bruice

  DOI：10.1016/s0960-894x(03)00119-7

  日期：2003.4

  Positively charged DNG oligonucleotide mixed sequences containing A/T bases were prepared by solid-phase synthesis. Synthesis proceeds in 3'-->5' direction and involves coupling of 3'-Fmoc protected thiourea in the presence of HgCl2/TEA with the corresponding 5'-amine of the growing oligo chain. DNG binding characteristics with complementary DNA and with itself have been evaluated. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Deoxynucleic guanidine
  作者：Hemavathi Challa、Thomas C Bruice

  DOI：10.1016/j.bmc.2003.12.043

  日期：2004.3

  The synthesis of purine nucleosides capable of making the guanidinium linkage is described for the first time starting from the corresponding 2'-deoxynucleosides. The positively charged mixed base DNG oligomer containing guanine was synthesized on solid-phase using CPG as support from 3' to 5' direction using the precursor building block nucleosides. (C) 2004 Elsevier Ltd. All rights reserved.