1-hydro-6-methoxy-9-(2'-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrimido[4,5-b]indol-4-one | 581798-90-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 1-hydro-6-methoxy-9-(2'-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrimido[4,5-b]indol-4-one
• 英文别名: 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methoxy-3H-pyrimido[4,5-b]indol-4-one
• CAS: 581798-90-5
• 化学式: C₁₆H₁₇N₃O₅
• 分子量: 331.328
• InChiKey: YOKMRJBGULPPRI-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-hydro-6-methoxy-9-(2'-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrimido[4,5-b]indol-4-one 在 吡啶 、 四氮唑 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 1-hydro-6-methoxy-9-(2'-deoxy-5'-O-dimethoxytrityl-β-D-erythro-pentofuranosyl-3-O'-cyanoethyl-N,N'-diisopropylphosphoramidite)-7H-pyrimido[4,5-b]indol-4-one
  参考文献：
  名称：

  Design of Base-Discriminating Fluorescent Nucleoside and Its Application to T/C SNP Typing

  摘要：

  We report a novel method for base detection using a base-discriminating fluorescent (BDF) nucleoside. We developed BDF probes containing methoxybenzodeazaadenine MDA and methoxybenzodeazainosine MDI, which give strong fluorescence only when the base on the complementary strand is cytosine and thymine, respectively. Thus, the MDA- and MDI-containing ODNs can be used as a very effective BDF probe for the detection of single base alterations, such as SNPs and point mutations. The present method using BDF probes is a very powerful tool for SNP typing that does not require any enzymes and time-consuming steps, and can avoid hybridization errors. In addition, a combination of MDA- and MDI-containing BDF probes facilitates the T/C SNP typing of a heterozygous sample.

  DOI：

  10.1021/ja035408l
• 作为产物：
  描述：

  4-chloro-6-methoxy-1H-pyrimido[4,5-b]indole 在 sodium hydroxide 、 sodium hydride 作用下， 以 乙醇 、 氯仿 、 乙腈 为溶剂， 反应 7.17h， 生成 1-hydro-6-methoxy-9-(2'-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrimido[4,5-b]indol-4-one
  参考文献：
  名称：

  Design of Base-Discriminating Fluorescent Nucleoside and Its Application to T/C SNP Typing

  摘要：

  We report a novel method for base detection using a base-discriminating fluorescent (BDF) nucleoside. We developed BDF probes containing methoxybenzodeazaadenine MDA and methoxybenzodeazainosine MDI, which give strong fluorescence only when the base on the complementary strand is cytosine and thymine, respectively. Thus, the MDA- and MDI-containing ODNs can be used as a very effective BDF probe for the detection of single base alterations, such as SNPs and point mutations. The present method using BDF probes is a very powerful tool for SNP typing that does not require any enzymes and time-consuming steps, and can avoid hybridization errors. In addition, a combination of MDA- and MDI-containing BDF probes facilitates the T/C SNP typing of a heterozygous sample.

  DOI：

  10.1021/ja035408l