3'-deoxy-3'-isocyanato-thymidine | 142387-25-5

• 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'-isocyanato-thymidine
• 英文别名: 3'-isocyanato-3'-deoxythymidine；1-[(2R,4S,5S)-5-(hydroxymethyl)-4-isocyanatooxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 142387-25-5
• 化学式: C₁₁H₁₃N₃O₅
• 分子量: 267.241
• InChiKey: HZPMEEXRJTZTNJ-DJLDLDEBSA-N

物化性质

• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3'-isocyanato-thymidine 在 ammonium hydroxide 作用下， 反应 0.25h， 以87%的产率得到3'-[(氨基羰基)氨基]-3'-脱氧胸苷
  参考文献：
  名称：

  Habich, Synthesis, 1992, # 4, p. 358 - 360

  摘要：

  DOI：
• 作为产物：
  描述：

  齐多夫定 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 3'-deoxy-3'-isocyanato-thymidine
  参考文献：
  名称：

  Habich, Synthesis, 1992, # 4, p. 358 - 360

  摘要：

  DOI：

文献信息

• Synthesis of 3′-Sugar- and Base-Modified Nucleotides and Their Application as Potent Chain Terminators in DNA Sequencing
  作者：Karen Stolze、Ulrich Koert、Sven Klingel、Gregor Sagner、Regina Wartbichler、Joachim W. Engels

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

  日期：1999.9.8

  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).