3',5'-diacetyl-N4-(TEMPO)-2'-deoxycytidine | 1201185-56-9

• 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',5'-diacetyl-N4-(TEMPO)-2'-deoxycytidine
• CAS: 1201185-56-9
• 化学式: C₂₂H₃₅N₄O₇
• 分子量: 467.542
• InChiKey: SGGWHIPEJYLEOI-YQVWRLOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  131.89
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3',5'-diacetyl-N4-(TEMPO)-2'-deoxycytidine 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 22.0h， 以100%的产率得到N4-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine
  参考文献：
  名称：

  Identification of Single-Base Mismatches in Duplex DNA by EPR Spectroscopy

  摘要：

  The spin-labeled nucleoside C-T, containing 2,2,6,6-tetramethyipiperidine-l-oxyL (TEMPO) conjugated to the exocyclic amino group of C, was used to detect single-base mismatches in duplex DNA for the first time by electron paramagnetic resonance (EPR) spectroscopy. Furthermore, the EPR spectra of the fully base-paired duplex (TC-G) and the mismatches (C-T-A, C-T-C, and C-T-T) were significantly different, showing that the probe can identify its base-pairing partner in DNA. At lower pH, the mobility of C-T-A, TC.C, and C-T-T became higher, consistent with increased protonation of the mismatched pairs. Although the duplexes for each of the three flanking sequences tested gave distinguishable EPR signals, the best discrimination between base pairs was achieved for sequences containing a flanking A-T base pair, in particular 5'-d(G(T)CA) and 5'-d(IICA). This study shows that minor structural variations in nucleic acids can be detected with carefully chosen spin [abets in conjunction with EPR spectroscopy.

  DOI：

  10.1021/ja905623k
• 作为产物：
  描述：

  tempamine 、 3',5'-Diacetyl-4-O-(2,4,6-triisopropylbenzenesulfonyl)-2'-deoxyuridine 以 二氯甲烷 为溶剂， 反应 22.0h， 以91%的产率得到3',5'-diacetyl-N4-(TEMPO)-2'-deoxycytidine
  参考文献：
  名称：

  Identification of Single-Base Mismatches in Duplex DNA by EPR Spectroscopy

  摘要：

  The spin-labeled nucleoside C-T, containing 2,2,6,6-tetramethyipiperidine-l-oxyL (TEMPO) conjugated to the exocyclic amino group of C, was used to detect single-base mismatches in duplex DNA for the first time by electron paramagnetic resonance (EPR) spectroscopy. Furthermore, the EPR spectra of the fully base-paired duplex (TC-G) and the mismatches (C-T-A, C-T-C, and C-T-T) were significantly different, showing that the probe can identify its base-pairing partner in DNA. At lower pH, the mobility of C-T-A, TC.C, and C-T-T became higher, consistent with increased protonation of the mismatched pairs. Although the duplexes for each of the three flanking sequences tested gave distinguishable EPR signals, the best discrimination between base pairs was achieved for sequences containing a flanking A-T base pair, in particular 5'-d(G(T)CA) and 5'-d(IICA). This study shows that minor structural variations in nucleic acids can be detected with carefully chosen spin [abets in conjunction with EPR spectroscopy.

  DOI：

  10.1021/ja905623k