7-(1'-carboxyethyl)guanine | 1227782-51-5

• 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: 7-(1'-carboxyethyl)guanine
• 英文别名: 7-(2-Carboxy-) ethylguanine；2-(2-amino-6-oxo-1H-purin-7-yl)propanoic acid
• CAS: 1227782-51-5
• 化学式: C₈H₉N₅O₃
• 分子量: 223.191
• InChiKey: UYURRUGZWCUQMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-碘丙酸 、 2'-脱氧鸟苷 以 异丁酰胺 为溶剂， 生成 7-(1'-carboxyethyl)guanine
  参考文献：
  名称：

  Detection of 7-(2′-Carboxyethyl)guanine but Not 7-Carboxymethylguanine in Human Liver DNA

  摘要：

  7-Carboxymethylguanine (7-CMGua) and 7-(2'-carboxyethyl)guanine (7-CEGua) are DNA adducts that potentially could be formed upon the metabolism of the carcinogenic nitrosamines N-nitrososarcosine (NSAR) and 3-(methylnitrosamino)propionic acid (MNPA), respectively, or from other sources such as nitrosation of glycine (7-CMGua) or reaction of DNA with acrylic acid (7-CEGua). Since both NSAR and MNPA have been detected in human urine and there are plausible sources of exposure to other precursors to these adducts, we analyzed human liver DNA for 7-CMGua and 7-CEGua, using liquid chromatography-electrospray ionization-tandem mass spectrometry-selected reaction monitoring (LC-ESI-MS/MS-SRM). Human hepatic DNA was mixed with [N-15(5)]7-CMGua and [N-15(5)]7-CEGua as internal standards and enzymatically hydrolyzed. The hydrolysate was partially purified by solid-phase extraction, and the resulting fraction was treated with acetyl chloride in methanol to convert 7-CMGua and 7-CEGua to their methyl esters. After a second solid-phase extraction, LC-ESI-MS/MS-SRM analysis was carried out using the transitions m/z 224 [M + H](+) -> m/z 164 [(M + H) - HCOOCH3](+) and m/z 238 [M + H](+) -> m/z 152 [BH](+) for the methyl esters of 7-CMGua and 7-CEGua, respectively. The method was sensitive, accurate, precise, and apparently free from artifact formation. 7-CEGua, as its methyl ester, was detected in all 24 human liver samples analyzed, mean +/- SD, 373 +/- 320 fmol/mu mol Gua (74.6 adducts per 10(9) nucleotides), range 17-1189 fmol/mu mol Gua, but the methyl ester of 7-CMGua was not detected in any sample. These results demonstrate the ubiquitous presence of 7-CEGua in human liver DNA. Acrylic acid may be a likely endogenous precursor to 7-CEGua.

  DOI：

  10.1021/tx100062v

文献信息

• METHOD OF MODIFYING NUCLEOTIDE CHAIN
  申请人：MATSUSHITA ELECTRIC INDUSTRIAL CO., LTD.

  公开号：EP1647592A1

  公开（公告）日：2006-04-19

  A method for modifying a nucleotide chain, which includes: allowing a catabolic enzyme specific to a nucleotide sequence containing a specific base such as hypoxanthine (Hx) to act on a nucleotide chain (I) to be modified having the above described nucleotide sequence containing a specific base on the 3'-terminal side thereof; and forming a functional group (for example, an aldehyde group) capable of binding to a desired modifier (for example, NH2R having an amino group) on the 3'-terminus of the nucleotide chain (I); so as to bind the above described modifier to the 3'-terminus of the nucleotide chain. Using a nucleotide chain as a modification target which has a nucleotide sequence containing a specific base acting as an enzyme substrate on its 3'-terminal side, this method enables decomposition of only the above described nucleotide sequence portion, thereby forming a functional group that reacts with a desired modifier and binds thereto. By this method, a nucleotide chain can directly be modified with a modifier, thereby easily labeling or conjugating the nucleotide chain. Further, when immobilization of a nucleotide chain is intended, stable and strong immobilization can be attained using a modifier as a linker.

  一种修饰核苷酸链的方法，包括让对含有特定碱基（如次黄嘌呤（Hx））的核苷酸序列具有特异性的分解酶作用于待修饰的核苷酸链（I），该核苷酸链具有在其 3'- 末端侧含有特定碱基的上述核苷酸序列；并在核苷酸链（I）的 3'末端形成能够与所需修饰剂（例如具有氨基的 NH2R）结合的官能团（例如醛基），从而将上述修饰剂结合到核苷酸链的 3'末端。使用核苷酸链作为修饰靶，该核苷酸链的 3'- 末端含有作为酶底物的特定碱基的核苷酸序列，这种方法可以只分解上述核苷酸序列部分，从而形成与所需修饰剂反应并结合的官能团。通过这种方法，核苷酸链可以直接被修饰剂修饰，从而方便地标记或连接核苷酸链。此外，当需要固定核苷酸链时，使用修饰剂作为连接剂可以实现稳定而牢固的固定。
• Method for modifying nucleotide chain
  申请人：Joko Shigeki

  公开号：US20070077629A1

  公开（公告）日：2007-04-05

  A method for modifying a nucleotide chain, which includes: allowing a catabolic enzyme specific to a nucleotide sequence containing a specific base such as hypoxanthine (Hx) to act on a nucleotide chain (I) to be modified having the above described nucleotide sequence containing a specific base on the 3′-terminal side thereof; and forming a functional group (for example, analdehyde group) capable of binding to a desired modifier (for example, NH 2 R having an amino group) on the 3′-terminus of the nucleotide chain (I); so as to bind the above described modifier to the 3′-terminus of the nucleotide chain. Using a nucleotide chain as a modification target which has a nucleotide sequence containing a specific base acting as an enzyme substrate on its 3′-terminal side, this method enables decomposition of only the above described nucleotide sequence portion, thereby forming a functional group that reacts with a desired modifier and binds thereto. By this method, a nucleotide chain can directly be modified with a modifier, thereby easily labeling or conjugating the nucleotide chain. Further, when immobilization of a nucleotide chain is intended, stable and strong immobilization can be attained using a modifier as a linker.
• METHOD FOR MODIFYING NUCLEOTIDE CHAIN
  申请人：JOKO Shigeki

  公开号：US20100291637A1

  公开（公告）日：2010-11-18

  A method for modifying a nucleotide chain, which includes: allowing a catabolic enzyme specific to a nucleotide sequence containing a specific base such as hypoxanthine (Hx) to act on a nucleotide chain (I) to be modified having the above described nucleotide sequence containing a specific base on the 3′-terminal side thereof; and forming a functional group (for example, an aldehyde group) capable of binding to a desired modifier (for example, NH 2 R having an amino group) on the 3′-terminus of the nucleotide chain (I); so as to bind the above described modifier to the 3′-terminus of the nucleotide chain. Using a nucleotide chain as a modification target which has a nucleotide sequence containing a specific base acting as an enzyme substrate on its 3′-terminal side, this method enables decomposition of only the above described nucleotide sequence portion, thereby forming a functional group that reacts with a desired modifier and binds thereto. By this method, a nucleotide chain can directly be modified with a modifier, thereby easily labeling or conjugating the nucleotide chain. Further, when immobilization of a nucleotide chain is intended, stable and strong immobilization can be attained using a modifier as a linker.
• US8129115B2
  申请人：——

  公开号：US8129115B2

  公开（公告）日：2012-03-06
• Detection of 7-(2′-Carboxyethyl)guanine but Not 7-Carboxymethylguanine in Human Liver DNA
  作者：Guang Cheng、Mingyao Wang、Peter W. Villalta、Stephen S. Hecht

  DOI：10.1021/tx100062v

  日期：2010.6.21

  7-Carboxymethylguanine (7-CMGua) and 7-(2'-carboxyethyl)guanine (7-CEGua) are DNA adducts that potentially could be formed upon the metabolism of the carcinogenic nitrosamines N-nitrososarcosine (NSAR) and 3-(methylnitrosamino)propionic acid (MNPA), respectively, or from other sources such as nitrosation of glycine (7-CMGua) or reaction of DNA with acrylic acid (7-CEGua). Since both NSAR and MNPA have been detected in human urine and there are plausible sources of exposure to other precursors to these adducts, we analyzed human liver DNA for 7-CMGua and 7-CEGua, using liquid chromatography-electrospray ionization-tandem mass spectrometry-selected reaction monitoring (LC-ESI-MS/MS-SRM). Human hepatic DNA was mixed with [N-15(5)]7-CMGua and [N-15(5)]7-CEGua as internal standards and enzymatically hydrolyzed. The hydrolysate was partially purified by solid-phase extraction, and the resulting fraction was treated with acetyl chloride in methanol to convert 7-CMGua and 7-CEGua to their methyl esters. After a second solid-phase extraction, LC-ESI-MS/MS-SRM analysis was carried out using the transitions m/z 224 [M + H](+) -> m/z 164 [(M + H) - HCOOCH3](+) and m/z 238 [M + H](+) -> m/z 152 [BH](+) for the methyl esters of 7-CMGua and 7-CEGua, respectively. The method was sensitive, accurate, precise, and apparently free from artifact formation. 7-CEGua, as its methyl ester, was detected in all 24 human liver samples analyzed, mean +/- SD, 373 +/- 320 fmol/mu mol Gua (74.6 adducts per 10(9) nucleotides), range 17-1189 fmol/mu mol Gua, but the methyl ester of 7-CMGua was not detected in any sample. These results demonstrate the ubiquitous presence of 7-CEGua in human liver DNA. Acrylic acid may be a likely endogenous precursor to 7-CEGua.