1'-(7-azaindolyl)-3',5'-di-O-(p-toluoyl)-2'deoxy-D-riboside | 124469-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1'-(7-azaindolyl)-3',5'-di-O-(p-toluoyl)-2'deoxy-D-riboside
• 英文别名: [(2R,3S,5R)-3-(4-methylbenzoyl)oxy-5-pyrrolo[2,3-b]pyridin-1-yloxolan-2-yl]methyl 4-methylbenzoate
• CAS: 124469-64-3
• 化学式: C₂₈H₂₆N₂O₅
• 分子量: 470.525
• InChiKey: JRRRJWKBLBSFHH-ISJGIBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1'-(7-azaindolyl)-3',5'-di-O-(p-toluoyl)-2'deoxy-D-riboside 在 磷酸三甲酯 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 Proton Sponge 、 三正丁胺 、 sodium methylate 、 一氯化碘 、 三丁基焦磷酸铵 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.29h， 生成
  参考文献：
  名称：

  Efforts toward Expansion of the Genetic Alphabet:  Optimization of Interbase Hydrophobic Interactions

  摘要：

  Six novel unnatural nucleobases have been characterized that form stable base pairs in duplex DNA, relying nor on hydrogen bonds, but rather on interbase hydrophobic interactions. These nucleobases are derivatives of the hydrophobic base pair between 7-azaindole (7AI) and isocarbostyril (ICS). Derivatives of 7AI and ICS were examined that have increased hydrophobic surface area, as well as increased polarizability. As observed with 7AI and ICS, these derivatives are recognized as substrates by Klenow fragment of Escherichia coli DNA polymerase I. The unnatural base pair between pyrrolopyrizine (PP) and C3-methylisocarbostyril (MICS) is enzymatically incorporated into DNA with high efficiency (k(cat)/K-M = 10(6) M-1 min(-1)) and moderate selectivity. These studies represent a significant step toward the generation of astable, orthogonal base pair that can be enzymatically incorporated into DNA with good fidelity.

  DOI：

  10.1021/ja0009931
• 作为产物：
  描述：

  7-氮杂吲哚 、 1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以66%的产率得到1'-(7-azaindolyl)-3',5'-di-O-(p-toluoyl)-2'deoxy-D-riboside
  参考文献：
  名称：

  Synthesis and fluorescence study of 7-azaindole in DNA oligonucleotides replacing a purine base

  摘要：

  The fluorescence spectroscopy of 7-azaindole (7(a)In) incorporated in DNA oligonucleotides is investigated. Incorporation of 7(a)In into DNA oligonucleotides is accomplished through standard solid-phase phosphoramidite chemistry. Fluorescence emission of the 7(a)In chromophore shifts slightly to the red (from 386 nm to 388 nm) upon glycosylation at the N-1 position, but its relative fluorescence quantum yield increases 23 times, from 0.023 to 0.53. Upon incorporation into DNA, the fluorescence emission of 7(a)In is greatly quenched with fluorescence quantum yields of 0.020 and 0.016 in single and double strand DNA, respectively. The fluorescence emission for 7(a)In in DNA oligonucleotides shifts to the blue with an emission maximum at 379 nm. Both the strong fluorescence quenching and the blue shift of the emission spectrum signify that 7(a)In is stacked with neighboring DNA bases in both single and double strand DNA. As the duplex DNA melts due to temperature increase, the fluorescence of the 7(a)In chromophore increases, indicating the transition from the less fluorescent duplex DNA to the more fluorescent single strand DNA. Since this fluorescent 7(a)In is a structural analog of purine, its fluorescence property may be utilized as a probe for studying nucleic acid structure and dynamics. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1386-1425(02)00004-5

文献信息

• Efforts toward the Expansion of the Genetic Alphabet:  Information Storage and Replication with Unnatural Hydrophobic Base Pairs
  作者：Anthony K. Ogawa、Yiqin Wu、Dustin L. McMinn、Jianquan Liu、Peter G. Schultz、Floyd E. Romesberg

  DOI：10.1021/ja9940064

  日期：2000.4.1

  whose pairing in duplex DNA is based on interbase hydrophobic interactions. We show that the stability and selectivity of such unnatural base pairs may be comparable to, or even exceed, that of native pairs. We also demonstrate that several unnatural base pairs are incorporated into DNA by Klenow fragment of Escherichia coli DNA polymerase I with an efficiency equivalent to that of native DNA synthesis

  对互补核碱基之间的链间氢键的忠实识别构成了遗传密码的基础。复制包含稳定第三个碱基对的 DNA 的能力将允许通过用第三个补充遗传字母表的现有两个碱基对来扩展 DNA 的信息内容。我们报告了非天然核碱基的优化，其在双链 DNA 中的配对基于碱基间疏水相互作用。我们表明，这种非天然碱基对的稳定性和选择性可能与天然碱基对相当，甚至超过。我们还证明了几个非天然碱基对通过大肠杆菌 DNA 聚合酶 I 的 Klenow 片段掺入 DNA，其效率与天然 DNA 合成的效率相当。而且，
• SEELA, F.;GUMBIOWSKI, R.;MUTH, H. -P.;BOURGEOIS, W., NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N-6, C. 1087-1088
  作者：SEELA, F.、GUMBIOWSKI, R.、MUTH, H. -P.、BOURGEOIS, W.

  DOI：——

  日期：——
• SEELA, F.;GUMBIOWSKI, R., HETEROCYCLES, 29,(1989) N, C. 795-805
  作者：SEELA, F.、GUMBIOWSKI, R.

  DOI：——

  日期：——
• Efforts toward Expansion of the Genetic Alphabet:  Optimization of Interbase Hydrophobic Interactions
  作者：Yiqin Wu、Anthony K. Ogawa、Markus Berger、Dustin L. McMinn、Peter G. Schultz、Floyd E. Romesberg

  DOI：10.1021/ja0009931

  日期：2000.8.1

  Six novel unnatural nucleobases have been characterized that form stable base pairs in duplex DNA, relying nor on hydrogen bonds, but rather on interbase hydrophobic interactions. These nucleobases are derivatives of the hydrophobic base pair between 7-azaindole (7AI) and isocarbostyril (ICS). Derivatives of 7AI and ICS were examined that have increased hydrophobic surface area, as well as increased polarizability. As observed with 7AI and ICS, these derivatives are recognized as substrates by Klenow fragment of Escherichia coli DNA polymerase I. The unnatural base pair between pyrrolopyrizine (PP) and C3-methylisocarbostyril (MICS) is enzymatically incorporated into DNA with high efficiency (k(cat)/K-M = 10(6) M-1 min(-1)) and moderate selectivity. These studies represent a significant step toward the generation of astable, orthogonal base pair that can be enzymatically incorporated into DNA with good fidelity.
• Synthesis and fluorescence study of 7-azaindole in DNA oligonucleotides replacing a purine base
  作者：Ke Wang、Sandra Stringfellow、Shiming Dong、Yugao Jiao、Hongtao Yu

  DOI：10.1016/s1386-1425(02)00004-5

  日期：2002.10

  The fluorescence spectroscopy of 7-azaindole (7(a)In) incorporated in DNA oligonucleotides is investigated. Incorporation of 7(a)In into DNA oligonucleotides is accomplished through standard solid-phase phosphoramidite chemistry. Fluorescence emission of the 7(a)In chromophore shifts slightly to the red (from 386 nm to 388 nm) upon glycosylation at the N-1 position, but its relative fluorescence quantum yield increases 23 times, from 0.023 to 0.53. Upon incorporation into DNA, the fluorescence emission of 7(a)In is greatly quenched with fluorescence quantum yields of 0.020 and 0.016 in single and double strand DNA, respectively. The fluorescence emission for 7(a)In in DNA oligonucleotides shifts to the blue with an emission maximum at 379 nm. Both the strong fluorescence quenching and the blue shift of the emission spectrum signify that 7(a)In is stacked with neighboring DNA bases in both single and double strand DNA. As the duplex DNA melts due to temperature increase, the fluorescence of the 7(a)In chromophore increases, indicating the transition from the less fluorescent duplex DNA to the more fluorescent single strand DNA. Since this fluorescent 7(a)In is a structural analog of purine, its fluorescence property may be utilized as a probe for studying nucleic acid structure and dynamics. (C) 2002 Elsevier Science B.V. All rights reserved.