(+)-trans-(5R,6R)-5-bromo-6-hydroxy-5,6-dihydrothymidine | 43179-29-9

• 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: (+)-trans-(5R,6R)-5-bromo-6-hydroxy-5,6-dihydrothymidine
• 英文别名: 5-Bromo-6-hydroxy-5,6-dihydrothymidine；(5R,6R)-5-bromo-6-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,3-diazinane-2,4-dione
• CAS: 43179-29-9
• 化学式: C₁₀H₁₅BrN₂O₆
• 分子量: 339.143
• InChiKey: QXTLVJPXEUPBNF-FZCTVIHWSA-N

物化性质

• 密度：
  1.830±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-trans-(5R,6R)-5-bromo-6-hydroxy-5,6-dihydrothymidine 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 ethyl N-<(5S,6S)-cis-(+)-5-hydroxy-5,6-dihydro-6-thymidyl>-L-methioninate
  参考文献：
  名称：

  胸苷环氧化物与胺和L-氨基酸乙酯的反应产物的立体结构

  摘要：

  研究了胸苷环氧化物（3）和（4）与胺和L-氨基酸乙酯的反应，并确定了产物的立体结构。

  DOI：

  10.1039/c39860001469
• 作为产物：
  描述：

  beta-胸苷 生成 (+)-trans-(5R,6R)-5-bromo-6-hydroxy-5,6-dihydrothymidine
  参考文献：
  名称：

  HARAYAMA, TAKASHI;YANADA, REIKO;TANAKA, MIHOKO;TAGA, TOORU;MACHIDA, KATSU+, J. CHEM. SOC. PERKIN TRANS. PT I,(1988) N 9, C. 2555-2562

  摘要：

  DOI：

文献信息

• Radiation-induced binding of 2,2,6,6-tetramethyl-1,4-piperidone-<i>N</i>-oxyl to thymidine in oxygen-free aqueous solutions. Isolation and characterization of the adducts
  作者：Maurice Berger、Jean Cadet、Jacques Ulrich

  DOI：10.1139/v85-002

  日期：1985.1.1

  Steady-state γ-radiolysis of deaerated aqueous solutions of thymidine has been carried out in the presence of 2,2,6,6-tetramethyl-1,4-piperidone-N-oxyl (TAN), a well-known radiosensitizing agent. The eight main radiation-induced TAN addition products to thymidine have been isolated and characterized by 1H and 13C nmr, cd, and fast-atom bombardment mass spectrometry measurements.

  已在 2,2,6,6-四甲基-1,4-哌啶酮-N-氧基 (TAN)（一种众所周知的放射增敏剂）存在下对脱气的胸苷水溶液进行稳态 γ-辐射分解。胸苷的八种主要辐射诱导的 TAN 加成产物已被分离出来，并通过 1H 和 13C nmr、cd 和快速原子轰击质谱测量进行表征。
• The repair of thymine and thymidine bromohydrins, models of damaged nucleic acids, by a copper(II) and ascorbic acid system
  作者：Reiko Yanada、Taishin Akiyama、Takashi Harayama、Kazuo Yanada、Haruo Meguri、Fumio Yoneda

  DOI：10.1039/c39890000238

  日期：——

  Bromohydrins (1), (3), (4), and (5), damaged products of thymine derivatives, were repaired smoothly to regenerate the original thymine derivatives when exposed to ascorbic acid in the presence of a catalytic amount of Cu2+ in water at room temperature.

  胸腺嘧啶衍生物的受损产物溴代醇（1），（3），（4）和（5）在催化量的Cu 2+存在下于抗坏血酸中被平滑修复，从而再生了原始的胸腺嘧啶衍生物。在室温下加水。
• On the repair of thymine and thymidine bromohydrins: A possible new model for the damage and repair of nucleic acids.
  作者：Takashi HARAYAMA、Reiko YANADA、Taishin AKIYAMA、Mihiko TANAKA、Yuki FUJITA、Fumio YONEDA

  DOI：10.1248/cpb.39.612

  日期：——

  Bromohydrins (2, 3, 4, and 5), oxidatively damaged products of thymine bases, were repaired on exposure to sunlight, heat, and/or some reagents to regenerate the thymine bases. A radical mechanism is proposed for the repair reaction with sunlight and heat. A hypothesis concerning the biological significance of thymidine in deoxyribonucleic acid is presented.

  胸腺嘧啶碱的氧化损伤产物溴代醇（2、3、4和5）在暴露于阳光，热和/或某些试剂的情况下被修复，以再生胸腺嘧啶碱。提出了一种自由基机理用于与阳光和热的修复反应。提出了关于胸苷在脱氧核糖核酸中的生物学意义的假设。
• Shaw, Anthony A.; Voituriez, Lucienne; Cadet, Jean, Journal of the Chemical Society. Perkin transactions II, 1988, p. 1303 - 1308
  作者：Shaw, Anthony A.、Voituriez, Lucienne、Cadet, Jean、Gregoli, Silvano、Symons, Martyn C.

  DOI：——

  日期：——
• Conformational and Electronic Properties of the Two <i>Cis </i>(5<i>S</i>,6<i>R</i>) and (5<i>R</i>,6<i>S</i>) Diastereoisomers of 5,6-Dihydroxy-5,6-dihydrothymidine:  X-ray and Theoretical Studies
  作者：Franck Jolibois、Lucienne Voituriez、André Grand、Jean Cadet

  DOI：10.1021/tx9501344

  日期：1996.1.1

  The structure of(+)-cis-(5S,6R)-5,6-dihydroxy-5,6-dihydrothymidine was obtained using X-ray crystallography [space group P2(1) with a = 10.130(3) Angstrom, b = 6.434(9) Angstrom, c = 11.02(5) Angstrom, and beta = 112.646(2)degrees]. The comparison of the two cis diastereoisomers of thymidine glycol (I,II) showed several structural and conformational differences. The solid state structures appear to be in agreement with the results of H-1 NMR studies which were carried out in aqueous solution. Conformational and electronic properties of the ground state of the molecules I and II were obtained using ab initio LSD-DFT theory. Only slight differences between the crystal structure and the optimized geometry are observed for each of the two oxidized nucleosides. On the other hand, molecules I and II exhibit significant differences in their electronic properties. In particular, the dipole moment of (5S,6R)-thymidine glycol (I) is twice smaller than that of the (5R,6S) diastereoisomer (II). It is noteworthy that these differences in the electronic properties between the two compounds may be related to changes in the rotameric population around the C4'-C5' bond. The repartition of the electrostatic potential is different in the two compounds. These observations lead to a better understanding of the structural changes when the above lesions are induced within a DNA molecule.