2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylisoquinolin-1-one | 300545-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylisoquinolin-1-one
• CAS: 300545-97-5
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: BKDHEUZHRCWMCG-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylisoquinolin-1-one 在 磷酸三甲酯 、 Proton Sponge 、 三正丁胺 、 三丁基焦磷酸铵 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.02h， 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：

  6-甲基-1(2H)-异喹啉酮 在 甲醇 、 sodium methylate 、 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylisoquinolin-1-one
  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

• 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.