2-[2-(4,4'-dimethoxytrityloxy)ethylsulfonyl]ethanol | 108783-01-3

• 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: 2-[2-(4,4'-dimethoxytrityloxy)ethylsulfonyl]ethanol
• 英文别名: 2-(4,4'-dimethoxytrityloxyethylsulfonyl)ethanol；2-O-(4,4'-dimethoxytrityl) sulfonyldiethanol；2-((2-(Bis(4-methoxyphenyl)(phenyl)methoxy)ethyl)sulfonyl)ethan-1-OL；2-[2-[bis(4-methoxyphenyl)-phenylmethoxy]ethylsulfonyl]ethanol
• CAS: 108783-01-3
• 化学式: C₂₅H₂₈O₆S
• mdl: MFCD00337749
• 分子量: 456.56
• InChiKey: BMUIOJXOMHOGTE-UHFFFAOYSA-N

物化性质

• 沸点：
  645.0±55.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[2-(4,4'-dimethoxytrityloxy)ethylsulfonyl]ethanol 在 四氮唑 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  A chemical 5′-phosphorylation of oligodeoxyribonucleotides that can be monitored by trityl cation release

  摘要：

  DOI：

  10.1016/s0040-4039(00)85043-1
• 作为产物：
  描述：

  2,2′-磺酰基双乙醇 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 作用下， 生成 2-[2-(4,4'-dimethoxytrityloxy)ethylsulfonyl]ethanol
  参考文献：
  名称：

  Oligo(2′-O-methylribonucleotides) and their derivatives: IV. Conjugates of oligo(2′-O-methylribonucleotides) with minor groove binders and intercalators: Synthesis, properties, and application

  摘要：

  Triplex forming 3'-protected pyrimidine oligo(2'-O-methylribonucleotides) containing minor groove binders (MGB) and triplex specific intercalator, benzoindoloquinoline (BIQ), at the 5'-terminus were synthesized. The resulting conjugates formed stable complexes with a target dsDNA due to the simultaneous binding to the minor and major grooves and BIQ intercalation. The dissociation constants and the thermal stability were evaluated for the conjugate complexes with the model dsDNA corresponding to the polypurine tract (PPT) of the nef and pol genes from the HIV proviral genome. The conjugation of oligo(2'-O-methylribonucleotides) with MGB and BIQ was shown to increase the stability of the triple complexes with dsDNA at pH 7.2 and 37A degrees C. Moreover, the intercalator accelerates the process of the complex formation. The dosedependent arrest of the in vitro transcription was demonstrated when a 780-bp DNA fragment containing the polypurine tract was transcribed under the control of T7 promoter in the presence of different concentrations of conjugates of oligo(2'-O-methylribonucleotides) containing MGB and BIQ.

  DOI：

  10.1134/s1068162013010081

文献信息

• Phosphorylating reagents and method of using the same
  申请人：CHIRON CORPORATION

  公开号：EP0304215A2

  公开（公告）日：1989-02-22

  Novel phosphorylating reagents are provided which are useful in DNA synthesis and purification procedures. The reagents are substituted phosphines which are particularly useful in the phosphorylation of nucleoside and solid supported oligonucleotides at the 5′-­hydroxyl position. Phosphorylation using these reagents is easily and accurately monitored colorimetrically.

  所提供的新型磷酸化试剂可用于 DNA 合成和纯化程序。这些试剂是取代的膦，特别适用于核苷和固体支持的寡核苷酸在 5′-羟基位置的磷酸化。使用这些试剂进行磷酸化时，可以用比色法轻松而准确地进行监测。
• Biologically active oligodeoxyribonucleotides—IX.1 Synthesis and anti-HIV-1 activity of hexadeoxyribonucleotides, TGGGAG, bearing 3′- and 5′-end-modification
  作者：Makoto Koizumi、Rika Koga、Hitoshi Hotoda、Kenji Momota、Toshinori Ohmine、Hidehiko Furukawa、Toshinori Agatsuma、Takashi Nishigaki、Koji Abe、Toshiyuki Kosaka、Shinya Tsutsumi、Junko Sone、Masakatsu Kaneko、Satoshi Kimura、Kaoru Shimada

  DOI：10.1016/s0968-0896(97)00161-2

  日期：1997.12

  We have determined that hexadeoxyribonucleotides (5'TGGGAG3'), with modified aromatic groups such as a trityl group at the 5'-end, have anti-HIV-1 activity in vitro. The 6-mer bearing a 3,4-dibenzyloxybenzyl (3,4-DBB) group at the 5'-end had the most potent activity and the least cytotoxicity. When the 3'-end of the 5'-(3,4-DBB)-modified 6-mer was substituted with a 2-hydroxyethylphosphate, a 2-hydroxyethylthiophosphate, or a methylphosphate group at the 3'-end, anti-HIV-1 activity increased. Moreover, among various 3'- and 5'-end-modified 6-mers that were tested, the 6-mer (R-95288) bearing a 3,4-DBB group at the 5'-end and a 2-hydroxyethylphosphate group at the 3'-end was the most stable, when incubated with mouse, rat, or human plasma. Therefore, R-95288 was chosen as the best candidate for possible use in therapy on the basis of its anti-HIV-1 activity. (C) 1997 Elsevier Science Ltd.
• Photomodulation of PS-modified oligonucleotides containing azobenzene substituent at pre-selected positions in phosphate backbone
  作者：Satyakam Patnaik、P. Kumar、B.S. Garg、R.P. Gandhi、K.C. Gupta

  DOI：10.1016/j.bmc.2007.08.042

  日期：2007.12

  A new protocol has been developed for incorporation of a photoisomerizable azobenzene moiety into synthetic stereo-enriched [R-p] and [S-p] PS-oligonucleotides. The azobenzene pendant is attached at pre-selected positions in internucleotidic phosphorothioate oligonucleotides of both [R-p] and [S-p] diastereomers using a novel reagent, N-iodoacetyl-p-aminoazobenzene, 1. The modified oligomers are purified on HPLC, characterized by LC-MS, and examined for their thermal and photoisomerization properties. The azobenzene moiety imparts greater stability to oligomer duplexes in (E) N=N con. guration as compared to (Z) configuration. The placement of the azobenzene pendant close to 5'-terminus (n - 1) and 3'-terminus of the modified PS-oligos contributes maximum stability to the duplex while a gradual decline in stability occurs with azobenzene moving toward middle of the duplex. Circular Dichroism studies reveal that the chiral environment at the phosphorus center of the PS-oligos does not alter the global conformation of the DNA duplex as such, suggesting conservation of conformation of the modified DNA strands. (c) 2007 Elsevier Ltd. All rights reserved.
• Recognition and Inhibition of HIV Integrase by Novel Dinucleotides
  作者：Michael Taktakishvili、Nouri Neamati、Yves Pommier、Suresh Pal、Vasu Nair

  DOI：10.1021/ja992528d

  日期：2000.6.1

  HIV integrase is involved in the integration of viral DNA into chromosomal DNA, a biological process that occurs by a sequence involving HIV DNA splicing and subsequent integration steps. in the quest for small nucleotide systems with nuclease stability of the internucleotide phosphate bond and critical structural features for recognition and inhibition of HIV-1 integrase, we have discovered novel, nuclease-resistant dinucleotides with defined base sequences that are inhibitors of this key viral enzyme. Synthetic methodologies utilized for the syntheses of the novel dinucleotides include an excellent new phosphorylating agent.
• Chemical phoshorylation of oligonucleotides and reactants used therefor
  申请人：Glen Research Corporation

  公开号：EP0816368B1

  公开（公告）日：2003-01-08