N³-(2-thiobenzoylethyl)uridine | 154153-59-0

• 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: N³-(2-thiobenzoylethyl)uridine
• 英文别名: S-[2-[3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxopyrimidin-1-yl]ethyl] benzenecarbothioate
• CAS: 154153-59-0
• 化学式: C₁₈H₂₀N₂O₇S
• 分子量: 408.432
• InChiKey: WNBQLVPYWOVIJM-DTZQCDIJSA-N

物化性质

• 沸点：
  642.3±65.0 °C(predicted)
• 密度：
  1.522±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  153
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N³-(2-thiobenzoylethyl)uridine 在 吡啶 、 咪唑 、 lithium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N³-ethyluridine tert-butyl disulfide
  参考文献：
  名称：

  二硫键稳定的RNA发夹的合成

  摘要：

  一个Ñ -3的RNA发夹的乙硫醇改性的尿苷已经合成，并通过固相亚磷酰胺化学结合在5'和3'末端，以通过二硫键交联提供增加的构象稳定性。

  DOI：

  10.1016/0040-4039(94)88309-2
• 作为产物：
  描述：

  尿嘧啶核苷 在 氢氟酸 、 sodium hydride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N³-(2-thiobenzoylethyl)uridine
  参考文献：
  名称：

  二硫键稳定的RNA发夹的合成

  摘要：

  一个Ñ -3的RNA发夹的乙硫醇改性的尿苷已经合成，并通过固相亚磷酰胺化学结合在5'和3'末端，以通过二硫键交联提供增加的构象稳定性。

  DOI：

  10.1016/0040-4039(94)88309-2

文献信息

• Design, Synthesis, and Analysis of Yeast tRNA^Phe Analogs Possessing Intra- and Interhelical Disulfide Cross-Links
  作者：Jay T. Goodwin、Scott E. Osborne、Emily J. Scholle、Gary D. Glick

  DOI：10.1021/ja960091t

  日期：1996.6.5

  Disulfide cross-links have been site-specifically incorporated into unmodified yeast tRNA(Phe) by total chemical synthesis. One cross-link is between positions 1 and 72 in the amino-acid acceptor stem, and it was prepared by replacing G1 and C72 with N-3-(thioethyl)uridine. A second cross-link is in the central D-region of yeast tRNA(Phe) between 11 and 25, and it was synthesized by replacing C11 and C25 with 2'-O-alkylthiol modified cytosine residues. Air oxidation to form the cross-link at both sites occurs in 12 h and is nearly quantitative. Analysis of the crosslinked products by native and denaturing PAGE along with Pb(II) cleavage experiments demonstrates that the crosslinked molecules are monomeric and suggests that the disulfide bridges do not significantly alter the structure of the modified tRNAs relative to the parent sequence. The finding that cross-link formation between thiol-derivatized residues correlates with the position of these groups in the crystal structure of native yeast tRNA(Phe) that the modifications apparently do not perturb native structure suggests that this methodology should be applicable to the study of RNA structure, dynamics, and folding.
• Synthesis of a disulfide stabilized RNA hairpin
  作者：Jay T. Goodwin、Gary D. Glick

  DOI：10.1016/0040-4039(94)88309-2

  日期：1994.3

  An N-3 ethylthiol-modified uridine has been synthesized and incorporated through solid-phase phosphoramidite chemistry at the 5′- and 3′-termini of an RNA hairpin to provide increased conformational stability via a disulfide cross-link.

  一个Ñ -3的RNA发夹的乙硫醇改性的尿苷已经合成，并通过固相亚磷酰胺化学结合在5'和3'末端，以通过二硫键交联提供增加的构象稳定性。