3-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]嘧啶并[1,2-a]嘌呤-10-酮 | 78880-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]嘧啶并[1,2-a]嘌呤-10-酮
• 英文名称: pyrimido<1,2-a>purin-10(3H)-one nucleoside
• 英文别名: 1,N²-(1-propenyl-3-ylidene)guanosine；3-β-D-erythro-pentofuranosylpyrimido[1,2-a]purin-10(3H)-one；3-(β-D-pentofuranosyl)pyrimido<1,2-a>purin-10(3H)-one；3-β-D-ribofuranosylpyrimido<1,2-a>purin-10(3H)-one；3-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimido[1,2-a]purin-10(3H)-one；Gma-rppo；3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimido[1,2-a]purin-10-one
• CAS: 78880-62-3
• 化学式: C₁₃H₁₃N₅O₅
• 分子量: 319.277
• InChiKey: RDEWUXRNVMVRBR-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]嘧啶并[1,2-a]嘌呤-10-酮 在 sodium tetrahydroborate 作用下， 生成 3-β-D-erythro-pentofuranosyl-5,6-dihydropyrimido[1,2-a]purin-10(3H)-one
  参考文献：
  名称：

  Development of Monoclonal Antibodies to the Malondialdehyde−Deoxyguanosine Adduct, Pyrimidopurinone¹

  摘要：

  Malondialdehyde (MDA), an endogenous product of lipid peroxidation and prostaglandin biosynthesis, is mutagenic in bacterial and mammalian cells and carcinogenic in rats. In order to determine whether MDA-modified bases are formed in nucleic acids in vivo, sensitive immunoassays to detect MDA-DNA and MDA-RNA adducts are being developed in our laboratory. Murine monoclonal antibodies reactive with the MDA-deoxyguanosine adduct 3-beta-D-erythro-pentofuranosylpyrimido[1,2-alpha]purin-10(3H)-one (M(1)G-R) were prepared and characterized. Several MDA-modified nucleosides and deoxynucleosides and structural analogs were synthesized and characterized and were compared as competitive inhibitors in enzymelinked immunosorbent assays (ELISAs). Less than 5 fmol of M(1)G in MDA-modified DNA was detected in a direct ELISA, and antibody binding to the modified DNA was competitively inhibited by free M(1)G-dR. DNA from Salmonella typhimurium treated with concentrations of MDA that induce reversion to histidine prototrophy was enzymatically digested, and M(1)G-dR was quantitated by competitive ELISA. Over a range of MDA concentrations from 10 to 40 mM, the level of M(1)G residues in bacterial DNA increased from 0.2 to 2.5/10(6) base pairs.

  DOI：

  10.1021/tx960120d
• 作为产物：
  描述：

  5,6,7,8-tetrahydro-11-formyl-3(β-D-ribofuranosyl)-6,8-epoxyethenopyrimido<1,2-a>purin-10(3H)-one 反应 1.0h， 以60%的产率得到3-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]嘧啶并[1,2-a]嘌呤-10-酮
  参考文献：
  名称：

  Reaction of malonaldehyde with nucleic acid. IV. Formation of pyrimido(1,2-a)purin-10(3H)-one nucleoside by thermal decomposition of diastereomers containing oxadiazabicyclononene residues linked to guanosine.

  摘要：

  在强酸性条件下，1, 1, 3, 3-四乙氧基丙烷与鸟嘌呤核苷反应，形成与鸟嘌呤碱相连的非对映氧二氮杂环壬烯残基。非对映异构体受热分解后，得到了嘧啶并[1, 2-a]嘌呤-10(3H)-酮核苷（3），收率很高。开发出了一种制备 3 的简便方法，其中包括非对映异构体的热分解过程。

  DOI：

  10.1248/cpb.39.515

文献信息

• Reaction of Malonaldehyde with Nucleic Acid. I. Formation of Fluorescent Pyrimido[1,2-<i>a</i>]purin-10(3<i>H</i>)-one Nucleosides
  作者：Hiroshi Seto、Taisuke Okuda、Tomoyuki Takesue、Tadashi Ikemura

  DOI：10.1246/bcsj.56.1799

  日期：1983.6

  The reaction of malonaldehyde under acidic conditions (pH 4.5) with guanosine 5′-monophosphate resulted in the formation of fluorescent 3-(β-D-ribofuranosyl)pyrimido[1,2-a]purin-10(3H)-one 5′-phosphate (3a). This adduct was also isolated from malonaldehyde-reacted RNA. The amount of 3a in the modified RNA was estimated to be 0.4 per cent by weight. The fluorescence spectrum of 3a (Ex max. 360 nm, Em

  丙二醛在酸性条件 (pH 4.5) 下与鸟苷 5'-单磷酸反应形成荧光 3-(β-D-呋喃核糖基)嘧啶基 [1,2-a]purin-10(3H)-one 5' -磷酸盐 (3a)。该加合物也从丙二醛反应的 RNA 中分离出来。经修饰的 RNA 中 3a 的含量估计为 0.4%（按重量计）。3a 的荧光光谱（Ex max. 360 nm，Em max. 500 nm）与具有相同类型基础结构的鸟嘌呤-和鸟苷-丙二醛加合物的荧光光谱相似。另一方面，在丙二醛与核酸聚合物的反应中也形成了另一种类型的荧光团（Ex max. 390 nm，Em max. 460 nm）。因此，至少两种不同类型的荧光团存在于丙二醛反应的核酸中。
• STRUCTURE OF A NEW MODIFIED NUCLEOSIDE FORMED BY GUANOSINE-MALONALDEHYDE REACTION
  作者：Hiroshi Seto、Kazuyuki Akiyama、Taisuke Okuda、Tsuyoshi Hashimoto、Tomoyuki Takesue、Tadashi Ikemura

  DOI：10.1246/cl.1981.707

  日期：1981.6.5

  A new modified nucleoside was formed by the reaction of guanosine with malonaldehyde under acidic condition. This compound emitted strong yellow fluorescence and was hydrolyzed by NaOH into guanosine and malonaldehyde. Its structure was determined to be 1,N2-(1-propenyl-3-ylidene)guanosine by the spectroscopic analysis.

  鸟苷与丙二醛在酸性条件下反应生成新的修饰核苷。该化合物发出强烈的黄色荧光，被氢氧化钠水解成鸟苷和丙二醛。通过光谱分析确定其结构为1,N2-(1-丙烯基-3-亚基)鸟苷。
• 一类内源性核苷M
  申请人：中南民族大学

  公开号：CN114213491A

  公开（公告）日：2022-03-22

  本发明属于化学合成领域，具体地，公开了一类内源性核苷M1dG及其衍生物的合成方法及其应用。所述内源性核苷M1dG及其衍生物的结构式为：戊糖上的取代基团如下：当R3＝H时，R1＝R2＝乙酰氧基、苯甲酰氧基或羟基；当R1＝R2＝R3时，R1＝乙酰氧基、苯甲酰氧基或羟基；当R2＝R3＝乙酰氧基时，R1为碘、溴、叠氮基或硫代乙酰基；当R2＝R3＝羟基时，R1为碘、溴、叠氮基或巯基；该合成使用对环境相对友好的AcOH作为溶剂，Ac2O为添加剂，1,1,3,3‑四甲氧基丙烷连接鸟苷上的亚氨基并发生环合，从而构建了一系列结构新颖的内源性核苷M1dG及其衍生物。实验过程操作简单、方便、收率高、化学选择性好，能高效地构建了一系列结构新颖的内源性核苷M1dG及其衍生物，为此类化合物的合成提供了新的方法与思路。
• Synthesis of Nucleoside and Nucleotide Analogues by Cyclization of the Guanine Base with 1,1,3,3-Tetramethoxypropane
  作者：Ting-Ting Deng、Yi-Bing Xie、Wen-Wu Sun、Jie Huang、Ting-Ting He、Ji-Kai Liu、Bin Wu

  DOI：10.1021/acs.orglett.2c03252

  日期：2022.10.28

  project, we aimed to address this issue by developing a highly efficient method to synthesize M1dG and its analogues. This method has wide functional group tolerance, as various guanine-based nucleosides and nucleotides are suitable for the reaction. Furthermore, large-scale and derivatization reactions were carried out to showcase the possibility for biochemists to study DNA damage and repair processes

  3-(2-Deoxy-β- d -erythropentofuranosyl)pyrimido[1,2- a ]purin-10(3 H )-one (M 1 dG) 是细菌和哺乳动物细胞中的一种内源性 DNA 加合物，可以探索为氧化应激的生物标志物。尽管如此，缺乏有效的方法来制备 M 1 dG 阻碍了对其生物合成和生物相关过程的深入研究。在这个项目中，我们旨在通过开发一种高效的方法来合成 M 1来解决这个问题dG 及其类似物。该方法具有广泛的官能团耐受性，因为各种基于鸟嘌呤的核苷和核苷酸都适用于该反应。此外，还进行了大规模和衍生化反应，以展示生物化学家未来研究 DNA 损伤和修复过程的可能性。
• Reaction of malondialdehyde with guanine nucleosides: formation of adducts containing oxadiazabicyclononene residues in the base-pairing region
  作者：Lawrence J. Marnett、Ashis K. Basu、Shawn M. O'Hara、Paul E. Weller、A. F. M. Maqsudur. Rahman、John P. Oliver

  DOI：10.1021/ja00266a065

  日期：1986.3