Tetra(thymidine phosphate) | 2476-57-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: Tetra(thymidine phosphate)
• 英文别名: (T_P)3T；5'-dTdTdTdT-3'；5'-d(TTTT)-3'；d(T4)；thymidylyl-(3'->5')-thymidylyl-(3'->5')-thymidylyl-(3'->5')-thymidine；[(2R,3S,5R)-3-[hydroxy-[[(2R,3S,5R)-3-[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] hydrogen phosphate
• CAS: 2476-57-5
• 化学式: C₄₀H₅₃N₈O₂₆P₃
• 分子量: 1154.82
• InChiKey: GDPJWJXLKPPEKK-SJAYXVESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  77
• 可旋转键数：
  20
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  442
• 氢给体数：
  9
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  Tetra(thymidine phosphate) 、 5'-O-dimethoxytritylthymidine 3'-H-phosphonate 生成 [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] [(2R,3S,5R)-3-[hydroxy-[[(2R,3S,5R)-3-[hydroxy-[[(2R,3S,5R)-3-[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate
  参考文献：
  名称：

  MAKINO, KEISUKE;MURAKAMI, AKIRA;NAGAHARA, SHUNJI;NAKATSUJI, YUNA;TAKEUCHI+, FREE RADICAL RES. COMMUN., 6,(1989) N, C. 311-316

  摘要：

  DOI：
• 作为产物：
  描述：

  5’-(4,4’-二甲氧基三苯基)-3’-脱氧胸苷 2’-(2-氰乙基-N,N-二异丙基)亚磷酰胺 在 吡啶盐酸盐 作用下， 以 乙腈 为溶剂， 生成 Tetra(thymidine phosphate)
  参考文献：
  名称：

  Nucleotides, Part LXII, Pyridinium Salts - An Effective Class of Catalysts for Oligonucleotide Synthesis

  摘要：

  Various pyridinium sails (see 1-9) have been tested as catalysts for the condensation step in the phosphoramidite approach of oligonucleotide synthesis. Pyridinium chloride (1) turned out to be the most effective activator, speeding up the condensation tremendously Pyridinium bromide (2) and 4-methylbenzenesulfonate (4) can also be regarded as powerful substitutes for the commonly used 1H-tetrazole. The acidic pK(a) of the pyridinium cation provides an optimal range for phosphoramidite activation, which is followed by a nucleophilic attack of the pyridine ring to give the P-pyridinio intermediate 11 as the most likely precursor of phosphite ester formation (Scheme). P-31-NMR Studies support this proposal indirectly.

  DOI：

  10.1002/(sici)1522-2675(19990609)82:6<879::aid-hlca879>3.0.co;2-5

文献信息

• New improvements in oligonucleotide synthesis by use of the p-nitrophenylethyl phosphate blocking group and its deprotection by DBU or DBN
  作者：Eugen Uhlmann、Wolfgang Pfleiderer

  DOI：10.1016/s0040-4039(00)71364-5

  日期：——

  Phosphate protection in the phosphotriester approach is improved by the new, versatile p-nitrophenylethyl group due to its stability in the condensation step and its clean removal by DBU and DBN respectively.

  新型的通用对硝基苯乙基增强了磷酸三酯方法中的磷酸盐保护功能，这是由于其在缩合步骤中的稳定性以及分别被DBU和DBN干净地去除的能力。
• Some developments in the phosphitetriester method for synthesis of oligonucleotides
  作者：R.L. Letsinger、E.P. Groody、N. Lander、T. Tanaka

  DOI：10.1016/0040-4020(84)85112-1

  日期：1984.1

  phosphite-triester synthesis of oligonucleotides. Use of this group enables one to simplify procedures for preparing active nucleoside phosphorochloridite reagents, to remove oligonucleotide phosphotriester intermediates intact from a solid support, and to conduct block syntheses in solution or on a silica support viaphosphite chemistry. Deprotection can be achieved by warming the trihaloethyl phosphotriesters with

  在寡核苷酸的亚磷酸酯-三酯合成中，1，1-二甲基-2，2，2-三氯乙基具有作为PO保护基的优点。使用该基团使人们能够简化制备活性核苷磷酰氯试剂的程序，从固体载体上完整地除去寡核苷酸磷酸三酯中间体，并通过亚磷酸酯化学方法在溶液中或在二氧化硅载体上进行嵌段合成。脱保护可以通过用三丁基膦加热三卤代乙基磷酸三酯来实现。与不溶性载体结合的低聚物的偶联和脱保护反应的高效率使该化学方法特别有吸引力。
• Oligonucleotide synthesis by the use of a 2-(levulinyloxymethyl)-5-nitrobenzoyl group as the novel base-labile protecting Group for the 5′-hydroxyl groups of ribonucleoside and 2′-deoxyribonucleoside 3′-phosphoramidites
  作者：Kazuo Kamaike、Hiroaki Takahashi、Takashi Kakinuma、Kimio Morohoshi、Yoshiharu Ishido

  DOI：10.1016/s0040-4039(97)01617-1

  日期：1997.9

  A novel 2-(levulinyloxymethyl)-5-nitrobenzoyl (LMNBz) protecting group for the 5′ position of nucleoside 3′-phosphoramidites was successfully applied to the solid-phase synthesis of both an oligodeoxyribonucleotide (TpTpT and TpTpTpT) and an octaribonucleotide in combination with a 2′-O-Thp protecting group (UpCpApGpUpUpGpG). The LMNBz group was simply unmasked due to its base-labile property by a

  一种新型的2-（乙酰丙酰氧基甲基）-5-硝基苯甲酰基（LMNBz）核苷3'-亚磷酰胺的5'位保护基团已成功地用于寡脱氧核糖核苷酸（TpTpT和TpTpTpTT）和八核糖核苷酸的固相合成带有2'- O -Thp保护基（UpCpApGpUpUpGpG）。LMNBz基团由于其对碱不稳定的特性而通过两步程序（即先用0.5 M的水合肼在1：4的乙酸-吡啶中处理，然后再用0.5 M的咪唑的乙腈处理）简单地将其掩盖。
• Phosphorylating Reagent-Free Synthesis of 5′-Phosphate Oligonucleotides by Controlled Oxidative Degradation of Their 5′-End
  作者：Corinne Sallamand、Audrey Miscioscia、Rémy Lartia、Eric Defrancq

  DOI：10.1021/ol300542s

  日期：2012.4.20

  The 5'-phosphorylated oligonucleotides (5'-pONs) are currently synthesized using expensive and sensitive modified phosphoramidite reagents. In this work, a simple, cost-effective, efficient, and automatable method is presented, based on the controlled oxidation of the 5'-terminal alcohol followed by a beta-elimination reaction. The latter reaction leads to the removal of the terminal 5'-nucleoside and subsequent formation of the 5'-phosphate moiety. Thus, chemical phosphorylation of oligonucleotides (DNA or RNA) is achieved without using modified phosphorarnidites.
• METHOD FOR LIQUID-PHASE SYNTHESIS OF NUCLEIC ACIDS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2921499B1

  公开（公告）日：2020-01-22