1-(2-deoxy-β-D-erythro-pentofuranosyl)-6,7-dimethyllumazine | 35777-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(2-deoxy-β-D-erythro-pentofuranosyl)-6,7-dimethyllumazine
• 英文别名: 1-(2'-deoxy-β-D-ribofuranosyl)-6,7-dimethyllumazine；6,7-Dimethyl-1-(2'-desoxy-β-D-ribofuranosyl)lumazin；6,7-dimethyl-1-(β-D-erythro-2-deoxy-pentofuranosyl)-1H-pteridine-2,4-dione
• CAS: 35777-72-1
• 化学式: C₁₃H₁₆N₄O₅
• 分子量: 308.294
• InChiKey: QHQNYTKBVDCJTL-DJLDLDEBSA-N

物化性质

• 密度：
  1.508±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.26
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  130.33
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-β-D-erythro-pentofuranosyl)-6,7-dimethyllumazine 在 ammonium hydroxide 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 49.0h， 生成 Ammonium-thymidylyl(3'-5')-1-(2'-desoxy-β-D-ribofuranosyl)-6,7-dimethyllumazin
  参考文献：
  名称：

  Bannwarth, Willi; Pfleiderer, Wolfgang, Liebigs Annalen der Chemie, 1980, # 1, p. 50 - 64

  摘要：

  DOI：
• 作为产物：
  描述：

  Hoffer's chlorosugar 在 ammonium sulfate 、 sodium methylate 、 六甲基二硅氮烷 作用下， 反应 6.0h， 生成 1-(2-deoxy-β-D-erythro-pentofuranosyl)-6,7-dimethyllumazine
  参考文献：
  名称：

  Nucleosides. LIV¹Synthesis and Properties of 3′-Azido- and 2′,3′-Dideoxy-6,7-diphenyllumazine Nucleosides

  摘要：

  The best approach for the synthesis of 1-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)lumazine (5) and its 6,7-dimethyl- (4) and 6,7-diphenyl derivatives (3) has been found in the interconversion of the corresponding 1-(2-deoxy-beta-D-threo-pentofuranosyl)-lumazines. Monomethoxytritylation at the 5'-position (1 7, 3 4, 4 9) followed by mesylation at the 3'-OH group and subsequent nucleophilic displacement by lithium azide afforded 1 9, 2 9 and 4 7 which were deprotected by acid treatment to give 3-5 in good yields. The syntheses of 1-(2,3-dideoxy-beta-D- glycero-pentofuranosyl)-6,7-diphenyllumazine (6) and its 6,7-dimethyl derivative (7) were achieved from 1-(2-deoxy-beta-D-erythro-pentofuranosyl)- 6,7-diphenyllumazine and the corresponding 6,7-dimethyllumazine (2 6) via their 5'-O-p-toluoyl- (2 0, 3 0), and 3'-deoxy-3'-iodo derivatives (2 4, 3 1) to form, after radical dehalogenation and final deprotection, 6 and 7. The newly synthesized lumazine nucleosides have been characterized by elemental analyses, UV- and NMR spectra.

  DOI：

  10.1080/15257779408013278

文献信息

• Energy Transfer within Oligonucleotides from a Lumazine (= Pteridine-2,4(1<i>H</i>,3<i>H</i>)-dione) Chromophore to Bathophenanthroline-ruthenium(II) Complexes
  作者：Willi Bannwarth、Wolfgang Pfleiderer、Francis Müller

  DOI：10.1002/hlca.19910740834

  日期：1991.12.11

  (1) and of a bathophenan-throline-ruthenium(II) complex into synthetic oligodeoxynucleotides is described. This combination represents a new energy-transfer system with the lumazine chromophore as donor and the Ru complex as acceptor within the nucleotide. The system can be measured by time-resolved fluorometry or by lifetime measurements of the lumazine fluorescence and bears the potential of a spectroscopic

  描述了将1-（2'-脱氧-β-D-核呋喃呋喃糖基）-6,7-二甲基azine嗪（1）和红酚-胆碱-钌（II）络合物化学插入到合成的寡脱氧核苷酸中。这种结合代表了一种新的能量转移系统，其中核苷酸内的发光分子是发色团生色团，而Ru络合物是受体。可以通过时间分辨荧光法或通过对azine嗪荧光的寿命测量来测量该系统，并且该系统具有光谱尺的潜力。
• Charubala, Ramamurthy; Bannwart, Willi; Pfleiderer, Wolfgang, Liebigs Annalen der Chemie, 1980, # 1, p. 65 - 79
  作者：Charubala, Ramamurthy、Bannwart, Willi、Pfleiderer, Wolfgang

  DOI：——

  日期：——