5'-O-胸苷酰 3'-O-(2'-脱氧腺苷)硫代磷酸酯 | 92127-73-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 中文名称: 5'-O-胸苷酰 3'-O-(2'-脱氧腺苷)硫代磷酸酯
• 中文别名: 5'-O-胸苷酰3'-O-(2'-脱氧腺苷)硫代磷酸酯
• 英文名称: 5'-dAT
• 英文别名: 1-[(2R,4S,5R)-5-[[[(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 92127-73-6
• 化学式: C₂₀H₂₆N₇O₉PS
• 分子量: 571.508
• InChiKey: XNGOOGOMEACAQT-DDLFOQJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  249
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  (2R,5S)-2-chloro-3,1-oxaza-2-phosphabicyclo[3.3.0]octane 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 5'-O-胸苷酰 3'-O-(2'-脱氧腺苷)硫代磷酸酯
  参考文献：
  名称：

  Stereo-enriched phosphorothioate oligodeoxynucleotides: synthesis, biophysical and biological properties

  摘要：

  Stereo-enriched [Rp] and [Sp]-phosphorothioate oligodeoxynucleotides are synthesized using oxazaphospholidine derivatized monomers. Three different designs of phosphorothioate oligodeoxynucleotides (PS-oligos), (i) stereo-enriched all-[Rp] or all-[Sp] PS-linkages, (ii) stereo-random mixture of PS-linkages, and (iii) segments containing certain number of stereo-enriched [Rp] and [Sp] PS-linkages ([Sp-Rp-Sp] or [Rp-Sp-Rp]), have been studied. Thermal melting studies of these PS-oligos with RNA complementary strands showed that the binding affinities are in the order [Rp] > [Sp-Rp-Sp] = [Rp-Sp-Rp] > stereo-random > [Sp]. Circular dichroism (CD) studies suggest that the stereochemistry of the PS-oligo does not affect the global conformation of the duplex. The in vitro nuclease stability of these PS-oligos is in the order [Sp] > [Sp-Rp-Sp], stereo-random > [Rp]. The RNase H activation is in the order [Rp] > stereo-random > [Rp-Sp-Rp] > [Sp] > [Sp-Rp-Sp]. Studies in a cancer cell Line of PS-oligos targeted to MDM2 mRNA showed that all oligos had similar biological activity under the experimental conditions employed. Protein- and enzyme-binding studies showed insignificant stereo-dependent binding to proteins. The [Sp] and [Sp-Rp-Sp] chimeric and stereo-random PS-oligos that contained a CpG motif showed higher cell proliferation than [Rp] PS-oligo of the same sequence. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00275-8

文献信息

• Acylphosphonates
  作者：Mitsuo Fujii、Kouji Ozaki、Mitsuo Sekine、Tsujiaki Hata

  DOI：10.1016/s0040-4020(01)81630-6

  日期：1987.1

  synthesized by a new method via dideoxyribonucleoside 2,2,2-trichloroethoxycarbonylphosphonates and aroylphosphonates. The conversion of dideoxyribonucleoside 2,2,2-trichloroethoxycarbonylphosphonates to dideoxyribonucleoside trimethylsilyl phosphites by treatment with Me3SiCl-Zn-acetylacetone proceeded with retention configuration at phosphorus. The silyl phosphite intermediates were converted to the phosphorothioates

  通过二脱氧核糖核苷2,2,2-三氯乙氧基羰基膦酸酯和芳酰基膦酸酯通过新方法合成了脱氧核糖核苷硫代磷酸酯。通过用Me 3 SiCl-Zn-乙酰丙酮处理，将双脱氧核糖核苷2,2,2-三氯乙氧基羰基膦酸酯转化为双脱氧核糖核苷三甲基甲硅烷基亚磷酸酯，在磷处具有保留构型。通过用硫原位处理将亚磷酸甲硅烷基酯中间体转化为硫代磷酸酯。通过n-BuNH 2的作用，很容易将芳酰基从8-11上除去，并通过单质硫处理原位转化为双脱氧核糖核苷硫代磷酸酯中的仅一种非对映异构体（Rp-构型）。
• N-pent-4-enoyl nucleosides: Application in the synthesis of support-bound and free oligonucleotide analogs by the H-phosphonate approach
  作者：Radhakrishnan P. Iyer、Theresa Devlin、Ivan Habus、Nan-Hui Ho、Dong Yu、Sudhir Agrawal

  DOI：10.1016/0040-4039(96)00066-4

  日期：1996.3

  N-pent-4-enoyl nucleoside H-phosphonates are versatile building blocks for the synthesis of support-bound and free oligonucleotide analogs.

  N-戊-4-烯酰基核苷H-膦酸酯是用于合成支持物结合的和游离的寡核苷酸类似物的通用结构单元。
• Stereo-enriched phosphorothioate oligodeoxynucleotides: synthesis, biophysical and biological properties
  作者：Dong Yu、Ekambar R. Kandimalla、Allysen Roskey、Qiuyan Zhao、Lihong Chen、Jiangdong Chen、Sudhir Agrawal

  DOI：10.1016/s0968-0896(99)00275-8

  日期：2000.1

  Stereo-enriched [Rp] and [Sp]-phosphorothioate oligodeoxynucleotides are synthesized using oxazaphospholidine derivatized monomers. Three different designs of phosphorothioate oligodeoxynucleotides (PS-oligos), (i) stereo-enriched all-[Rp] or all-[Sp] PS-linkages, (ii) stereo-random mixture of PS-linkages, and (iii) segments containing certain number of stereo-enriched [Rp] and [Sp] PS-linkages ([Sp-Rp-Sp] or [Rp-Sp-Rp]), have been studied. Thermal melting studies of these PS-oligos with RNA complementary strands showed that the binding affinities are in the order [Rp] > [Sp-Rp-Sp] = [Rp-Sp-Rp] > stereo-random > [Sp]. Circular dichroism (CD) studies suggest that the stereochemistry of the PS-oligo does not affect the global conformation of the duplex. The in vitro nuclease stability of these PS-oligos is in the order [Sp] > [Sp-Rp-Sp], stereo-random > [Rp]. The RNase H activation is in the order [Rp] > stereo-random > [Rp-Sp-Rp] > [Sp] > [Sp-Rp-Sp]. Studies in a cancer cell Line of PS-oligos targeted to MDM2 mRNA showed that all oligos had similar biological activity under the experimental conditions employed. Protein- and enzyme-binding studies showed insignificant stereo-dependent binding to proteins. The [Sp] and [Sp-Rp-Sp] chimeric and stereo-random PS-oligos that contained a CpG motif showed higher cell proliferation than [Rp] PS-oligo of the same sequence. (C) 2000 Elsevier Science Ltd. All rights reserved.