3-methyladenine | 60192-57-6

• 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: 3-methyladenine
• 英文别名: 3-MA；3-Methyladenine；3-methyl-7H-purin-6-imine
• CAS: 60192-57-6
• 化学式: C₆H₇N₅
• mdl: MFCD02685598
• 分子量: 149.155
• InChiKey: ZPBYVFQJHWLTFB-UHFFFAOYSA-N

物化性质

• 蒸汽压力：
  1.20e-09 mmHg
• 碰撞截面：
  126.3 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyladenine 、 (1S,2R,4aS,8aR)-1-((E)-5-Bromo-3-methyl-pent-3-enyl)-1,2,5,5-tetramethyl-octahydro-naphthalen-4a-ol 以 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 生成 (1S,2R,4aS,8aR)-1-[(E)-5-(6-Imino-3-methyl-3,6-dihydro-purin-7-yl)-3-methyl-pent-3-enyl]-1,2,5,5-tetramethyl-octahydro-naphthalen-4a-ol
  参考文献：
  名称：

  海洋海绵嘌呤（+）-阿格拉西敏-A和（+）-阿格拉西敏-B的合成和绝对构型

  摘要：

  从海洋海绵Agelas mauritiana分离的（+）-agelasimine-A和（+）-agelasimine-B，与腺嘌呤相关的双环二萜类化合物的第一个总合成已通过高度立体选择性的途径实现。基于目前的结果，已经定义了两种生物碱的绝对构型，分别如立体式（+）- 1a和（+）- 1b所示。

  DOI：

  10.1016/s0040-4020(97)10120-x
• 作为产物：
  描述：

  三甲基碘化亚砜 、 ((2R)-2,7-diamino-1-((9-(4-hydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)amino)-6-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-pyrrolo[1,2-a]indol-9-yl)methyl carbamate 在 盐酸 、 propynol 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以14%的产率得到1-methyladenine
  参考文献：
  名称：

  用还原活化的丝裂霉素C修饰脱氧核糖核酸。修饰核苷酸的结构。

  摘要：

  Mitomycin C (MMC) 在经过 Pd 催化氢化还原激活后，与脱氧核糖核酸 (DNA) 结合。通过与核酸酶 P1 的酶促水解，将修改后的 DNA 提取出来，并使用高效液相色谱法 (HPLC) 分离和纯化了三种修饰核苷酸，分别命名为 MG-1、MG-2 和 MA。对质子核磁共振 (1H-NMR) 和紫外 (UV) 光谱的分析，以及对这些修饰核苷酸的酸性和酶促水解物的研究表明，MG-1 和 MG-2 是与去氧鸟苷酸-MMC 结合的产物，结合位点在 mitosene 的第 1 位和鸟苷体的一个杂原子上。对于产物 MA，提出了与腺苷体的类似结合。化学转化（甲基化、重氮化和硫酮化）被用来明确确定嘌呤碱基的结合位点。结合位点被确定为 MG-1 的鸟苷 N2 原子、MG-2 的鸟苷 O6 原子以及 MA 的腺苷 N6 原子。因此，这三种修饰核苷酸被总结为 1, 2-trans-2, 7-二氨基-1-(N2-去氧鸟苷酸) mitosene (MG-1)、2, 7-二氨基-1-(O6-去氧鸟苷酸) mitosene (MG-2) 和 2, 7-二氨基-1-(N6-去氧腺苷酸) mitosene (MA)。这些相同的修饰核苷酸在用 MMC 处理的大鼠肝脏提取的 DNA 中被确认存在。

  DOI：

  10.1248/cpb.31.861

文献信息

• Modification of deoxyribonucleic acid with reductively activated mitomycin C. Structures of modified nucleotides.
  作者：YUICHI HASHIMOTO、KOICHI SHUDO、TOSHIHIKO OKAMOTO

  DOI：10.1248/cpb.31.861

  日期：——

  Mitomycin C (MMC) binds to deoxyribonucleic acid (DNA) after its reductive activation by catalytic hydrogenation with Pd on charcoal. Three modified nucleotides, named MG-1, MG-2 and MA, were isolated and purified by high performance liquid chromatography (HPLC) from the modified DNA after enzymatic hydrolysis to 5'-nucleotides with nuclease P1. Analysis of the proton nuclear magnetic resonance (1H-NMR) and ultraviolet (UV) spectra, and studies of the acid and enzymatic hydrolysates of these modified nucleotides suggested that MG-1 and MG-2 are deoxyguanylic acid-MMC adducts bound at position 1 of mitosene and a heteroatom of the guanine moiety. Analogous binding to an adenine moiety is proposed for the adduct, MA. Chemical transformations (methylation, diazotization and thioketonization) were used to unambiguously determine the binding sites of the purine bases. The binding sites were identified as the N2 atom of guanine for MG-1, the O6 atom of guanine for MG-2, and the N6 atom of adenine for MA. Thus, these three modified nucleotides were concluded to be 1, 2-trans-2, 7-diamino-1-(N2-deoxyguanylyl) mitosene (MG-1), 2, 7-diamino-1-(O6-deoxyguanylyl) mitosene (MG-2), and 2, 7-diamino-1-(N6-deoxyadenylyl) mitosene (MA). These same modified nucleotides were identified in DNA extracted from the livers of rats treated with MMC.

  Mitomycin C (MMC) 在经过 Pd 催化氢化还原激活后，与脱氧核糖核酸 (DNA) 结合。通过与核酸酶 P1 的酶促水解，将修改后的 DNA 提取出来，并使用高效液相色谱法 (HPLC) 分离和纯化了三种修饰核苷酸，分别命名为 MG-1、MG-2 和 MA。对质子核磁共振 (1H-NMR) 和紫外 (UV) 光谱的分析，以及对这些修饰核苷酸的酸性和酶促水解物的研究表明，MG-1 和 MG-2 是与去氧鸟苷酸-MMC 结合的产物，结合位点在 mitosene 的第 1 位和鸟苷体的一个杂原子上。对于产物 MA，提出了与腺苷体的类似结合。化学转化（甲基化、重氮化和硫酮化）被用来明确确定嘌呤碱基的结合位点。结合位点被确定为 MG-1 的鸟苷 N2 原子、MG-2 的鸟苷 O6 原子以及 MA 的腺苷 N6 原子。因此，这三种修饰核苷酸被总结为 1, 2-trans-2, 7-二氨基-1-(N2-去氧鸟苷酸) mitosene (MG-1)、2, 7-二氨基-1-(O6-去氧鸟苷酸) mitosene (MG-2) 和 2, 7-二氨基-1-(N6-去氧腺苷酸) mitosene (MA)。这些相同的修饰核苷酸在用 MMC 处理的大鼠肝脏提取的 DNA 中被确认存在。
• Muravich-Aleksandr, Kh. L.; Pernikoza, V. G.; Girshovich, M. Z., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 11, p. 2094 - 2099
  作者：Muravich-Aleksandr, Kh. L.、Pernikoza, V. G.、Girshovich, M. Z.、Ragozina, T. N.

  DOI：——

  日期：——
• Method of Screening for Plant Defense Activators, Plant Defense Activators, and Method of Enhancing Immune Response
  申请人：Kuchitsu Kazuyuki

  公开号：US20150141252A1

  公开（公告）日：2015-05-21

  A method of screening for a plant defense activator, which enhances an immune response of a plant, from at least one candidate substance includes: contacting a plant cell in which a jasmonic acid-dependent defense pathway and a salicylic acid-dependent defense pathway of a plant defense system are capable of working independently from each other, with a candidate substance; contacting the plant cell with a trigger material that induces an immune response; and assaying the plant cell after contacting with the trigger material based on an index representing an immune response, to select a target substance that enhances an immune response of the plant. A method of enhancing an immune response of a plant includes use of a specific compound, and a plant immune response enhancer includes the specific compound.
• US9739767B2
  申请人：——

  公开号：US9739767B2

  公开（公告）日：2017-08-22
• [EN] METHOD OF SCREENING FOR PLANT DEFENSE ACTIVATORS, PLANT DEFENSE ACTIVATORS, AND METHOD OF ENHANCING IMMUNE RESPONSE<br/>[FR] PROCÉDÉ DE CRIBLAGE POUR DES ACTIVATEURS DE DÉFENSE VÉGÉTALE, ACTIVATEURS DE DÉFENSE VÉGÉTALE ET PROCÉDÉ D'AUGMENTATION DE LA RÉPONSE IMMUNITAIRE
  申请人：UNIV TOKYO SCI EDUC FOUND

  公开号：WO2012029539A1

  公开（公告）日：2012-03-08

  A method of screening for a plant defense activator, which enhances an immune response of a plant, from at least one candidate substance includes: contacting a plant cell in which a jasmonic acid-dependent defense pathway and a salicylic acid-dependent defense pathway of a plant defense system are capable of working independently from each other, with a candidate substance; contacting the plant cell with a trigger material that induces an immune response; and assaying the plant cell after contacting with the trigger material based on an index representing an immune response, to select a target substance that enhances an immune response of the plant. A method of enhancing an immune response of a plant includes use of a specific compound, and a plant immune response enhancer includes the specific compound.