N'-{9-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-N,N-dimethyl-formamidine | 172481-05-9

• 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: N'-{9-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-N,N-dimethyl-formamidine
• 英文别名: 9-(β-D-2-deoxy-5'-OTBS-ribofuranosyl)-6-N,N-dimethylformamidylpurine；N'-[9-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]purin-6-yl]-N,N-dimethylmethanimidamide
• CAS: 172481-05-9
• 化学式: C₁₉H₃₂N₆O₃Si
• 分子量: 420.587
• InChiKey: ZCSKHDDMEHSPKY-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-azido-1-bromo-hept-2-ene 、 N'-{9-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-N,N-dimethyl-formamidine 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以60%的产率得到N'-{9-[4-(7-azido-hept-2-enyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-N,N-dimethyl-formamidine
  参考文献：
  名称：

  Synthesis of 3′-O-fluorescently mono-modified reversible terminators and their uses in sequencing-by-synthesis

  摘要：

  Next-generation sequencing (NGS) technologies recently developed are now used for study of genomes from various organisms. Sequencing-by-synthesis (SBS) is a key strategy in the NGS. The SBS uses nucleotides so-called dual-modified reversible terminators (DRTs) in which bases are labeled with fluorophores and 3'-OH is protected with a reversibly cleavable chemical group, respectively. In this study, we examined the possibility of performing SBS with mono-modified reversible terminators (MRTs), in which the reversible blocking group on the 3'-OH plays a dual role as a fluorescent signal report as well as a chemical protection. We studied cyclic reversible termination by using two MRTs (dA and dT), wherein the modifications were two different fluorophores and cleavable to regenerate a free 3'-OH. We here demonstrated that SBS could be achieved with incorporation of MRTs by a DNA polymerase and correct base-calls based on the two different colors from the fluorophores. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.040