O⁶-(2-Hydroxyethyl)guanine | 78014-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: O⁶-(2-Hydroxyethyl)guanine
• 英文别名: 2-[(2-Amino-7h-purin-6-yl)oxy]ethanol
• CAS: 78014-96-7
• 化学式: C₇H₉N₅O₂
• 分子量: 195.181
• InChiKey: BXWLIVQJPQLQDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O⁶-(2-Hydroxyethyl)guanine 在 tetrafluoroboric acid 、 sodium nitrite 作用下， 反应 4.0h， 生成 2-fluoro-O⁶-(2'-hydroxyethyl)hypoxanthine
  参考文献：
  名称：

  Chemical transformation/derivatization of O6-methyl- and O6-(hydroxyethyl)guanine for detection by GC-EC/MS

  摘要：

  In this project we set out to make an important class of DNA adducts, comprising O6-alkyl and O6-(hydroxyalkyl)guanines, susceptible to sensitive detection by GC-EC/MS. While existing literature indicated that pentafluorobenzylation would be useful for the ring NH site on these compounds, how to best overcome the polarity of the exocyclic NH2 and OH groups, without losing the O6-alkyl moiety, was less clear. Working with O6-methylguanine and O6-(2'-hydroxyethyl)guanine as representative analytes, we found that the NH2 group could be converted into fluoro without loss of the O6 substituent. For the OH group, a comparison of several derivatives (OR') led to R' = tert-butyl as the best choice at this stage. The latter work, especially via NMR, also allowed exact structural assignments to be made for the N7 and N9 pentafluorobenzyl isomeric derivatives that formed. Of these R' derivatives, the N7 isomers migrated slower on silica-TLC, had higher GC retention times, had lower responses by GC-EC/MS, and were preferentially destroyed as the GC column aged. However, the N9 isomer was slower on TLC when the OH was not derivatized. This behavior was rationalized using a concept of ''polar footprint'' for the derivatives. The concept also seemed to explain the puzzling GC-EC/MS behavior of some related compounds in our laboratory. Apparently the polar footprint should be minimized in designing derivatives for trace detection by GC-EC/MS.

  DOI：

  10.1021/ac00069a021
• 作为产物：
  描述：

  α-hydroperoxy-N-nitrosomorpholine 、 2'-脱氧鸟苷 在 三(2-羰基乙基)磷盐酸盐 、 盐酸 、 sodium hydroxide 作用下， 以 乙腈 、 水 为溶剂， 反应 0.5h， 生成 N(7)-羟基乙基鸟嘌呤 、 O⁶-(2-Hydroxyethyl)guanine
  参考文献：
  名称：

  致癌物N-亚硝基吗啉的代谢产物重氮离子与核苷嘌呤和DNA的直接反应产物

  摘要：

  已合成了许多衍生自3-羟基-N-亚硝基吗啉的重氮离子的嘌呤核苷和核碱基加合物作为二甲基缩醛。在大多数情况下，将它们转化为醛，或者在两种情况下，将其转化为醛，用温和的酸处理，以生成标准品，用于定量研究上述强力致癌物N的代谢产物对嘌呤核苷和DNA的烷基化作用。-亚硝基吗啉。在许多条件下，就其分解倾向而言，已表征了所得核碱基乙氧基乙醛（EA）加合物的稳定性。与苯并咪唑模型的先前表征的加合物相比，该稳定性通常是无例外的。嘌呤核苷和DNA上加合物的沉积在反应中进行了定量，在该反应中，3-膦基过氧化氢-N-亚硝基吗啉在21±2°C下被水溶性膦还原为羟基代谢物。加合物的谱图与从无环二烷基亚硝胺的简单α-羟基代谢产物观察到的高度相似，双链DNA反应中三种最丰富的乙氧基乙醛（EA）加合物为N7-EA-Gua〜O 6-EA-Gua> N3-EA-Ade。对于主要产物，对于核苷和DNA加合物，已经确定了由最初形

  DOI：

  10.1021/tx100093a

文献信息

• Optical performance humidity dependency improving agent for cellulose acylate film
  申请人：Nagura Masato

  公开号：US20110262661A1

  公开（公告）日：2011-10-27

  An optical performance humidity dependency improving agent for cellulose acylate film, which contains a compound having a nucleic acid base skeleton, is capable of preventing the fluctuation of Re and Rth of the film against the humidity change in usage environments.
• US9145417B2
  申请人：——

  公开号：US9145417B2

  公开（公告）日：2015-09-29
• Products of the Direct Reaction of the Diazonium Ion of a Metabolite of the Carcinogen <i>N</i>-Nitrosomorpholine with Purines of Nucleosides and DNA
  作者：Charles N. Zink、Nicolas Soissons、James C. Fishbein

  DOI：10.1021/tx100093a

  日期：2010.7.19

  major products in the cases of both the nucleoside and DNA adducts. The rates of formation of HE adducts are accelerated in DNA, relative to the nucleosides in the cases of the N7-EA-Ade, N7-EA-Gua, and O6-EA-Gua adducts by factors of 7, 14, and 54, respectively. The initial rates of depurination of the N3-EA-Ade, N7-EA-Gua, and N7-EA-Gua adducts have also been quantified, and they are unexceptional in

  已合成了许多衍生自3-羟基-N-亚硝基吗啉的重氮离子的嘌呤核苷和核碱基加合物作为二甲基缩醛。在大多数情况下，将它们转化为醛，或者在两种情况下，将其转化为醛，用温和的酸处理，以生成标准品，用于定量研究上述强力致癌物N的代谢产物对嘌呤核苷和DNA的烷基化作用。-亚硝基吗啉。在许多条件下，就其分解倾向而言，已表征了所得核碱基乙氧基乙醛（EA）加合物的稳定性。与苯并咪唑模型的先前表征的加合物相比，该稳定性通常是无例外的。嘌呤核苷和DNA上加合物的沉积在反应中进行了定量，在该反应中，3-膦基过氧化氢-N-亚硝基吗啉在21±2°C下被水溶性膦还原为羟基代谢物。加合物的谱图与从无环二烷基亚硝胺的简单α-羟基代谢产物观察到的高度相似，双链DNA反应中三种最丰富的乙氧基乙醛（EA）加合物为N7-EA-Gua〜O 6-EA-Gua> N3-EA-Ade。对于主要产物，对于核苷和DNA加合物，已经确定了由最初形
• Chemical transformation/derivatization of O6-methyl- and O6-(hydroxyethyl)guanine for detection by GC-EC/MS
  作者：Chingchen S. Chiu、Manasi. Saha、Amir. Abushamaa、Roger W. Giese

  DOI：10.1021/ac00069a021

  日期：1993.11.1

  In this project we set out to make an important class of DNA adducts, comprising O6-alkyl and O6-(hydroxyalkyl)guanines, susceptible to sensitive detection by GC-EC/MS. While existing literature indicated that pentafluorobenzylation would be useful for the ring NH site on these compounds, how to best overcome the polarity of the exocyclic NH2 and OH groups, without losing the O6-alkyl moiety, was less clear. Working with O6-methylguanine and O6-(2'-hydroxyethyl)guanine as representative analytes, we found that the NH2 group could be converted into fluoro without loss of the O6 substituent. For the OH group, a comparison of several derivatives (OR') led to R' = tert-butyl as the best choice at this stage. The latter work, especially via NMR, also allowed exact structural assignments to be made for the N7 and N9 pentafluorobenzyl isomeric derivatives that formed. Of these R' derivatives, the N7 isomers migrated slower on silica-TLC, had higher GC retention times, had lower responses by GC-EC/MS, and were preferentially destroyed as the GC column aged. However, the N9 isomer was slower on TLC when the OH was not derivatized. This behavior was rationalized using a concept of ''polar footprint'' for the derivatives. The concept also seemed to explain the puzzling GC-EC/MS behavior of some related compounds in our laboratory. Apparently the polar footprint should be minimized in designing derivatives for trace detection by GC-EC/MS.