1-(2-O-tert-butyldimethylsilyl-3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl)uracil

• 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: 1-(2-O-tert-butyldimethylsilyl-3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl)uracil
• 英文别名: TBDMS(-2)[N(iPr)2P(OCH2CH2CN)(-3)][DMT(-5)]L-Ribf(a)-uracil-1-yl；3-[[(2S,3S,4S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• 化学式: C₄₅H₆₁N₄O₉PSi
• 分子量: 861.06
• InChiKey: SKNLXHRBXYGJOC-CRNVMSACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.51
• 重原子数：
  60
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  L-核糖 在 吡啶 、 咪唑 、 盐酸 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.0h， 生成 1-(2-O-tert-butyldimethylsilyl-3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5-O-(4,4'-dimethoxytrityl)-α-L-ribofuranosyl)uracil
  参考文献：
  名称：

  Synthesis and RNA-selective hybridization of α-l-ribo- and β-d-lyxo-configured oligonucleotides

  摘要：

  Three alpha-L-ribofuranosyl analogues of RNA nucleotides (alpha-L-RNA analogues) have been synthesized and incorporated into oligonucleotides using the phosphoramide approach on an automated DNA synthesizer. The 4'-C-hydroxymethyl-alpha-L-ribofuranosyl thymine monomer was furthermore synthesized. Relative to the unmodified duplexes, incorporation of a single a-L-RNA monomer into a DNA strand leads to reduced thermal stability of duplexes with DNA complements but unchanged thermal stability of duplexes with RNA complements, whereas incorporation of more than one alpha-L-RNA monomer lead to moderately decreased thermal stability also of duplexes with RNA complements. Efficient hybridization with an RNA complement and no melting transition with a DNA complement were observed with stereoregular chimeric oligonucleotides composed of a mixture of alpha-L-RNA and affinity enhancing alpha-L-LNA monomers (alpha-L-ribo-configured locked nucleic acid). Furthermore, duplexes formed between oligodeoxynucleotides containing an alpha-L-RNA monomer and complementary RNA were good substrates for Escherichia coli RNase H. RNA-selective hybridization was also achieved by the incorporation of 1-(4-C-hydroxymethyl-beta-D-lyxofuranosyl)thymine monomers into a DNA strand, whereas stable duplexes were formed with both complementary DNA and RNA when these monomers were incorporated into an RNA strand. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.007

文献信息

• Synthesis and RNA-selective hybridization of α-l-ribo- and β-d-lyxo-configured oligonucleotides
  作者：Gilles Gaubert、B. Ravindra Babu、Stefan Vogel、Torsten Bryld、Birte Vester、Jesper Wengel

  DOI：10.1016/j.tet.2005.12.007

  日期：2006.3

  Three alpha-L-ribofuranosyl analogues of RNA nucleotides (alpha-L-RNA analogues) have been synthesized and incorporated into oligonucleotides using the phosphoramide approach on an automated DNA synthesizer. The 4'-C-hydroxymethyl-alpha-L-ribofuranosyl thymine monomer was furthermore synthesized. Relative to the unmodified duplexes, incorporation of a single a-L-RNA monomer into a DNA strand leads to reduced thermal stability of duplexes with DNA complements but unchanged thermal stability of duplexes with RNA complements, whereas incorporation of more than one alpha-L-RNA monomer lead to moderately decreased thermal stability also of duplexes with RNA complements. Efficient hybridization with an RNA complement and no melting transition with a DNA complement were observed with stereoregular chimeric oligonucleotides composed of a mixture of alpha-L-RNA and affinity enhancing alpha-L-LNA monomers (alpha-L-ribo-configured locked nucleic acid). Furthermore, duplexes formed between oligodeoxynucleotides containing an alpha-L-RNA monomer and complementary RNA were good substrates for Escherichia coli RNase H. RNA-selective hybridization was also achieved by the incorporation of 1-(4-C-hydroxymethyl-beta-D-lyxofuranosyl)thymine monomers into a DNA strand, whereas stable duplexes were formed with both complementary DNA and RNA when these monomers were incorporated into an RNA strand. (c) 2005 Elsevier Ltd. All rights reserved.