5'-monomethoxytritylamino-2',5'-dideoxythymidine-3'-O-succinate | 278168-49-3

• 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'-monomethoxytritylamino-2',5'-dideoxythymidine-3'-O-succinate
• 英文别名: 5'-MMT-amino-5'-deoxythymidine 3'-monosuccinate；4-[(2R,3S,5R)-2-[[[(4-methoxyphenyl)-diphenylmethyl]amino]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-4-oxobutanoic acid
• CAS: 278168-49-3
• 化学式: C₃₄H₃₅N₃O₈
• 分子量: 613.667
• InChiKey: PQMUUMQDJYZWBP-ZGIBFIJWSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5'-monomethoxytritylamino-2',5'-dideoxythymidine-3'-O-succinate 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 13.0h， 生成 6-N,N-Dibenzoyl-9-<2-deoxy-3-O-methanesulphonyl-5-O-(4-monomethoxytrityl)-β-D-threo-pentofuranosyl>adenine
  参考文献：
  名称：

  Solid-Phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide mixed sequences

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(03)00119-7
• 作为产物：
  描述：

  4-甲氧基三苯基氯甲烷 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 5'-monomethoxytritylamino-2',5'-dideoxythymidine-3'-O-succinate
  参考文献：
  名称：

  带正电的脱氧核胍 (DNG) 的固相合成束缚 Hoechst 33258 类似物：通过同时小槽结合的三链和双链稳定

  摘要：

  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

  DOI：

  10.1021/ja031557s

文献信息

• Novel oligonucleotide analogues containing a morpholinoamidine unit
  作者：Sonia Pérez-Rentero、Javier Alguacil、Jordi Robles

  DOI：10.1016/j.tet.2008.11.069

  日期：2009.2

  were devised as new cationic units in oligonucleotides, by combining morpholino-nucleosides (to simplify the nomenclature, we will use the term morpholino-nucleosides to refer to nucleoside analogues in which the ribose ring was transformed into a morpholine) with internucleoside guanidines. Here, methodology was developed to synthesize oligonucleotides containing morpholinoamidines formed by morpholino-uridine

  通过结合吗啉代核苷（为简化命名，我们将使用吗啉代核苷一词来指代其中核糖环被转化为吗啉的核苷类似物）与核苷间胍，将吗啉代am啶设计为寡核苷酸中的新阳离子单元。在此，开发了合成包含由吗啉代尿苷和5'-氨基-5'-脱氧胸苷形成的吗啉代am的寡核苷酸的方法。吗啉代am是通过Alloc-吗啉代碳硫代酰胺与5'-氨基核苷酸树脂的固相反应和Mukaiyama的试剂活化而产生的。两个14聚体合成了包含单个吗啉代am的寡核苷酸，并通过形成DNA双螺旋和三螺旋来研究它们的亲和特性。双工通过3'单元略微稳定，但如果位于内部，则不稳定。值得注意的是，三重链在pH 7.0下显着稳定。
• Solid-phase synthesis of oligomeric deoxynucleic-thiourea (DNT) and deoxynucleic S -methylthiourea (DNmt): a neutral/polycationic analogue of DNA
  作者：Dev P Arya、Thomas C Bruice

  DOI：10.1016/s0960-894x(00)00085-8

  日期：2000.4

  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.
• 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.
• 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
• 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.