(2R,3S,5R)-2-Hydroxymethyl-5-(3-prop-1-ynyl-pyrrolo[2,3-b]pyridin-1-yl)-tetrahydro-furan-3-ol | 300545-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: (2R,3S,5R)-2-Hydroxymethyl-5-(3-prop-1-ynyl-pyrrolo[2,3-b]pyridin-1-yl)-tetrahydro-furan-3-ol
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-(3-prop-1-ynylpyrrolo[2,3-b]pyridin-1-yl)oxolan-3-ol
• CAS: 300545-95-3
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: VDOUNOZELCBVCS-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-2-Hydroxymethyl-5-(3-prop-1-ynyl-pyrrolo[2,3-b]pyridin-1-yl)-tetrahydro-furan-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(3-prop-1-ynyl-pyrrolo[2,3-b]pyridin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  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：

  1'-(7-azaindolyl)-3',5'-di-O-(p-toluoyl)-2'deoxy-D-riboside 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium methylate 、 一氯化碘 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.27h， 生成 (2R,3S,5R)-2-Hydroxymethyl-5-(3-prop-1-ynyl-pyrrolo[2,3-b]pyridin-1-yl)-tetrahydro-furan-3-ol
  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

文献信息

• Enzymatic Phosphorylation of Unnatural Nucleosides
  作者：Yiqin Wu、Ming Fa、Eunju Lee Tae、Peter G. Schultz、Floyd E. Romesberg

  DOI：10.1021/ja028050m

  日期：2002.12.1

  In an effort to expand the genetic alphabet, a number of unnatural, predominantly hydrophobic, nucleoside analogues have been developed which pair selectively in duplex DNA and during enzymatic synthesis. Significant progress has been made toward the efficient in vitro replication of DNA containing these base pairs. However, the in vivo expansion of the genetic alphabet will require that the unnatural

  为了扩大遗传字母表，已经开发了许多非天然的、主要是疏水性的核苷类似物，它们在双链 DNA 中和酶促合成过程中选择性地配对。在含有这些碱基对的 DNA 的体外有效复制方面取得了重大进展。然而，基因字母表的体内扩展将要求非天然三磷酸核苷在细胞内以足够的浓度用于 DNA 复制。我们报告了我们为开发基于核苷补救酶的非自然体内核苷磷酸化途径所做的初步努力。该途径的第一步由黑腹果蝇核苷激酶催化，该激酶催化核苷磷酸化为相应的单磷酸酯。
• 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.