胸苷溴代醇 | 43179-28-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 胸苷溴代醇
• 英文名称: (-)-trans-(5S,6S)-5-bromo-6-hydroxy-5,6-dihydrothymidine
• 英文别名: Thymidine bromohydrin；(5S,6S)-5-bromo-6-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,3-diazinane-2,4-dione
• CAS: 43179-28-8
• 化学式: C₁₀H₁₅BrN₂O₆
• 分子量: 339.143
• InChiKey: QXTLVJPXEUPBNF-NLFXGDPDSA-N

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：

  胸苷溴代醇 在 叔丁醇 作用下， 以 水 为溶剂， 反应 50.5h， 生成 5-羟甲基脱氧尿苷
  参考文献：
  名称：

  无氧水溶液中 2,2,6,6-四甲基-1,4-哌啶酮-N-氧基与胸苷的辐射诱导结合。加合物的分离和表征

  摘要：

  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。

  DOI：

  10.1139/v85-002
• 作为产物：
  描述：

  beta-胸苷 生成 胸苷溴代醇
  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

• 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。
• Stereostructures of reaction products of thymidine epoxides with amines and L-amino acid ethyl esters
  作者：Takashi Harayama、Reiko Yanada、Tooru Taga、Katsunosuke Machida、Jean Cadet、Fumio Yoneda

  DOI：10.1039/c39860001469

  日期：——

  Reaction of thymidine epoxides, (3) and (4), with amines and L-amino acid ethyl esters was investigated and the stereostructures of products were determined.

  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。
• 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.
• Harayama, Takashi; Yanada, Reiko; Tanaka, Mihoko, Journal of the Chemical Society. Perkin transactions I, 1988, p. 2555 - 2562
  作者：Harayama, Takashi、Yanada, Reiko、Tanaka, Mihoko、Taga, Tooru、Machida, Katsunosuke、et al.

  DOI：——

  日期：——