3'-deoxy-3'-{{{{6-[(trifluoroacetyl)amino]hexyl}amino}carbonyl}amino}thymidine | 251557-13-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-deoxy-3'-{{{{6-[(trifluoroacetyl)amino]hexyl}amino}carbonyl}amino}thymidine
• 英文别名: 2,2,2-trifluoro-N-[6-[[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]carbamoylamino]hexyl]acetamide
• CAS: 251557-13-8
• 化学式: C₁₉H₂₈F₃N₅O₆
• 分子量: 479.456
• InChiKey: WWTPKRSZGTWJBU-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3'-{{{{6-[(trifluoroacetyl)amino]hexyl}amino}carbonyl}amino}thymidine 在 三正丁胺 、 碘 、 三丁基焦磷酸铵 作用下， 以 1,4-二氧六环 、 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 3'-{{[(6-aminohexyl)amino]carbonyl}amino}-3'-deoxythymidine 5'-triphosphate
  参考文献：
  名称：

  Synthesis of 3′-Sugar- and Base-Modified Nucleotides and Their Application as Potent Chain Terminators in DNA Sequencing

  摘要：

  Two 3'-modified and three base-modified ddNTPs were synthesized and tested with several DNA polymerases for incorporation activity. Starting from 3'-azido-3'-deoxythymidine (AZT; 1), we were able to produce 3'-deoxy-3'-isocyanato-thymidine and 3'-deoxy-3'-isothiocyanatothymidine (3 and 4, resp,) in a rapid synthesis based on the solid-support approach (Scheme 1). These 3'-functionalities could be used to attach a spacer molecule via urea and thiourea groups, respectively. Since the thus-obtained tethered nucleotides 7 and 8 can be used to label with fluorescent dyes (cf. Scheme 5), they are convenient building blocks for practical applications in DNA sequencing. Furthermore, we synthesized, via 14 (Scheme 2), 17 (Scheme 3), and 19 (Scheme 4), the N-4-modified dideoxycytidine 5'-triphosphate dye derivatives 22, 23, and 24, respectively, with different lengths of linkers between the base residue and the dye (Scheme). Base-specific termination for the derivatives 22 and 23 was demonstrated (Fig. 2a and 2b).

  DOI：

  10.1002/(sici)1522-2675(19990908)82:9<1311::aid-hlca1311>3.0.co;2-z
• 作为产物：
  描述：

  齐多夫定 在 polymer-bound triphenylphosphine 作用下， 以 1,4-二氧六环 为溶剂， 生成 3'-deoxy-3'-{{{{6-[(trifluoroacetyl)amino]hexyl}amino}carbonyl}amino}thymidine
  参考文献：
  名称：

  Synthesis of 3′-Sugar- and Base-Modified Nucleotides and Their Application as Potent Chain Terminators in DNA Sequencing

  摘要：

  Two 3'-modified and three base-modified ddNTPs were synthesized and tested with several DNA polymerases for incorporation activity. Starting from 3'-azido-3'-deoxythymidine (AZT; 1), we were able to produce 3'-deoxy-3'-isocyanato-thymidine and 3'-deoxy-3'-isothiocyanatothymidine (3 and 4, resp,) in a rapid synthesis based on the solid-support approach (Scheme 1). These 3'-functionalities could be used to attach a spacer molecule via urea and thiourea groups, respectively. Since the thus-obtained tethered nucleotides 7 and 8 can be used to label with fluorescent dyes (cf. Scheme 5), they are convenient building blocks for practical applications in DNA sequencing. Furthermore, we synthesized, via 14 (Scheme 2), 17 (Scheme 3), and 19 (Scheme 4), the N-4-modified dideoxycytidine 5'-triphosphate dye derivatives 22, 23, and 24, respectively, with different lengths of linkers between the base residue and the dye (Scheme). Base-specific termination for the derivatives 22 and 23 was demonstrated (Fig. 2a and 2b).

  DOI：

  10.1002/(sici)1522-2675(19990908)82:9<1311::aid-hlca1311>3.0.co;2-z