4-oxo-non-2-enal | 89186-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-oxo-non-2-enal
• 英文别名: 4-oxo-2-nonenal；4-oxononenal；4-ONE；ONE；4-Hydroxy-2,3-nonadienal；4-oxonon-2-enal
• CAS: 89186-13-0
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: SEPPVOUBHWNCAW-UHFFFAOYSA-N

物化性质

• 沸点：
  258.1±23.0 °C(Predicted)
• 密度：
  0.933±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-oxo-non-2-enal 在 吡啶 、 甲醇 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 5'-O-(4,4'-dimethoxytrityl)-7-(2-oxoheptyl)-1,N2-etheno-2'-deoxyguanosine
  参考文献：
  名称：

  Comparison of the in Vitro Replication of the 7-(2-Oxoheptyl)-1,N²-etheno-2′-deoxyguanosine and 1,N²-Etheno-2′-deoxyguanosine Lesions by Sulfolobus solfataricus P2 DNA Polymerase IV (Dpo4)

  摘要：

  Oligonucleotides were synthesized containing the 7-(2-oxoheptyl)-etheno-dGuo adduct, which is derived from the reaction of dGuo and the lipid peroxidation product 4-oxo-2-nonenal. The in vitro replication of 7-(2-oxoheptyl)-etheno-dGuo by the model Y-family polymerase Sulfolobus solfataricus P2 DNA Polymerase IV (Dpo4) was examined in two sequences. The extension products were sequenced using an improved LC-ESI-MS/MS protocol developed in our laboratories, and the results were compared to that of the 1,N-2-etheno-dGuo adduct in the same sequence contexts. Both etheno adducts were highly miscoding when situated in 5'-TXG-3' local sequence contexts with <4% of the extension products being derived from error-free bypass. The major extension products resulted from the misinsertion of Ade opposite the adduct and a one-base deletion. The major extension products from replication of the etheno lesions in a 5'-CXG-3' local sequence context were the result of misinsertion of Ade, a one-base deletion, and error-free bypass. Other minor extension products were also identified. The 7-(2-oxoheptyl)etheno-dGuo lesion resulted in a larger frequency of misinsertion of Ade, whereas the 1,N-2-etheno-dGuo gave more of the one-base deletion product. Conformational studies of duplex DNA containing the 7-(2oxoheptyl)-etheno-dGuo in a 5'-TXG-3' sequence context by NMR indicated the presence of a pH-dependent conformational transition, likely involving the glycosyl bond at the adducted guanosine; the pK(a) for this transition was lower than that observed for the 1,N-2-epsilon-dGuo lesion. However, the 7-(2-oxoheptyl)-etheno-dGuo lesion, the complementary Cyt, and both flanking base pairs remained disordered at all pH values, which is attributed to the presence of the hydrophobic heptyl group of the 7-(2-oxoheptyl)etheno-dGuo lesion. The altered pK(a) value and the structural disorder at the 7-(2-oxoheptyl)-etheno-dGuo lesion site, as compared to the same sequence containing the 1,N-2-etheno-dGuo, may contribute to higher frequency of misinsertion of Ade.

  DOI：

  10.1021/tx100082e
• 作为产物：
  描述：

  4-hydroxy-2-nonenal diethyl acetal 在 盐酸 、 manganese(IV) oxide 、 柠檬酸 作用下， 生成 4-oxo-non-2-enal
  参考文献：
  名称：

  通过脂质过氧化的新产物4-氧代-2-壬烯醛对2'-脱氧鸟苷进行共价修饰。

  摘要：

  通过液相色谱/质谱（LC / MS）检测到2-脱氧鸟苷（dGuo）与13-氢过氧亚油酸反应的两种主要产物（加合物A和B）。当在亚油酸和脂氧合酶存在下孵育dGuo时，加合物A和B也是酶促形成的主要产物。加合物A和B的质谱碎片图谱表明已引入了对核苷的独特修饰。这导致表征了作为亚油酸氢过氧化物的主要分解产物的新型双功能亲电子试剂4-氧代-2-壬烯醛。在随后的研究中，发现加合物A是取代的ethano dGuo加合物，它是三种异构体（A（1）-A（3））的混合物，所有这些异构体都分解成加合物B。加合物A（1）是3-（2-deoxy-beta-D-erythropentafuranosyl）-3,5,6，7-tetrahydro-6-hydroxy-7-（庚烷-2-one）-9H-的半缩醛形式咪唑并[1，2-α嘌呤-9-一]。加合物A（2）和A（3）是开链酮形式的非对映异构体。加合物B是取代的乙二氧基

  DOI：

  10.1021/tx990034o

文献信息

• Application of Screening Experimental Designs to Assess Chromatographic Isotope Effect upon Isotope-Coded Derivatization for Quantitative Liquid Chromatography–Mass Spectrometry
  作者：Szabolcs Szarka、Katalin Prokai-Tatrai、Laszlo Prokai

  DOI：10.1021/ac501309s

  日期：2014.7.15

  Isotope effect may cause partial chromatographic separation of labeled (heavy) and unlabeled (light) isotopologue pairs. Together with a simultaneous matrix effect, this could lead to unacceptable accuracy in quantitative liquid chromatography–mass spectrometry assays, especially when electrospray ionization is used. Four biologically relevant reactive aldehydes (acrolein, malondialdehyde, 4-hydroxy-2-nonenal

  同位素效应可能导致标记（重）和未标记（轻）同位素对的部分色谱分离。再加上同时存在的基质效应，这可能导致定量液相色谱-质谱分析的准确性无法接受，尤其是在使用电喷雾电离时。四种生物相关的反应性醛（丙烯醛、丙二醛、4-羟基-2-壬烯醛和 4-氧代-2-壬烯醛）用轻质或重质（d 3 -、13 C 6 -、15 N 2 - 或15 ñ 4-标记) 2,4-二硝基苯肼并用作模型化合物以评估色谱同位素效应。为了在各种梯度反相液相色谱条件下综合评估轻/重对之间的保留时间差异，主要色谱参数（固定相、流动相 pH 值、温度、有机溶剂和梯度斜率）和不同同位素标记由多个解决方案解决。 - 使用包括不对称 (Addelman) 和 Plackett-Burman 方案的实验设计进行因子筛选，然后进行统计评估。结果证实，避免色谱同位素效应的最有效方法是使用15 N 或13C 标记代替氘标记，而色谱参数没有普遍影响。使用氘与15
• Substrate Specificity and Inhibitor Sensitivity of Rabbit 20α-Hydroxysteroid Dehydrogenase
  作者：Satoshi Endo、Yuki Arai、Akira Hara、Yukio Kitade、Yasuo Bunai、Ossama El-Kabbani、Toshiyuki Matsunaga

  DOI：10.1248/bpb.b13-00342

  日期：——

  reduced the 3-keto group of only 5α-dihydrosteroids with 17β- or 20α/β-hydroxy group among 3-ketosteroids. In contrast, the enzyme reversibly and efficiently catalyzed the reduction of various 17- and 20-ketosteroids, including estrogen precursors (dehydroepiandrosterone, estrone and 5α-androstan-3β-ol-17-one) and tocolytic 5β-pregnane-3,20-dione. In addition to the progesterone inactivation, the formation

  在这项研究中，我们检查了兔20α-羟类固醇脱氢酶（AKR1C5）的底物特异性和抑制剂敏感性，该酶在孕激素失活终止妊娠中发挥作用。AKR1C5在3-酮类固醇中仅还原具有17β-或20α/β-羟基的5α-二氢类固醇的3-酮基。相比之下，该酶可逆地有效地催化各种17-和20-酮类固醇的还原，包括雌激素前体（脱氢表雄酮，雌酮和5α-雄烷-3β-ol-17-one）和解卵5β-孕烯3,20- dione。除孕激素失活外，AKR1C5的雌激素形成和生育溶性类固醇的代谢可能与其在兔分娩中的作用有关。AKR1C5还还原了各种非甾族羰基化合物，包括靛红，C型利钠肽受体和4-oxo-2-nonenal的拮抗剂，表明其在控制生物活性靛红和细胞毒性醛的解毒中的作用。AKR1C5被山茱emp醇和槲皮素等黄酮类化合物有效地和竞争性地抑制，表明其活性受摄入的黄酮类化合物的影响。
• Rabbit 3-hydroxyhexobarbital dehydrogenase is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D2, and other endogenous and xenobiotic carbonyl compounds
  作者：Satoshi Endo、Toshiyuki Matsunaga、Atsuko Matsumoto、Yuki Arai、Satoshi Ohno、Ossama El-Kabbani、Kazuo Tajima、Yasuo Bunai、Shigeru Yamano、Akira Hara、Yukio Kitade

  DOI：10.1016/j.bcp.2013.08.024

  日期：2013.11

  for NADP(H) over NAD(H) at a physiological pH of 7.4. In the NADPH-linked reduction, 3HBD showed broad substrate specificity for a variety of quinones, ketones and aldehydes, including 3-, 17- and 20-ketosteroids and prostaglandin D(2), which were converted to 3alpha-, 17beta- and 20alpha-hydroxysteroids and 9alpha,11beta-prostaglandin F(2), respectively. Especially, alpha-diketones (such as isatin

  3-羟基己异巴比妥脱氢酶（3HBD）催化将NAD（P）（+）链接的3-羟基己异巴比妥氧化为3-羟基己异巴比妥。该酶被认为是异生物醇和某些羟基类固醇的脱氢酶，但其生理功能仍然未知。我们已经纯化了兔3HBD，分离了其cDNA，并检查了其对辅酶和底物的特异性，反应方向性和组织分布。3HBD是醛酮还原酶（AKR）超家族的成员（AKR1C29），并且在7.4的生理pH值下，NADP（H）优于NAD（H）。在与NADPH相关的还原反应中，3HBD对多种醌，酮和醛（包括3-，17-和20-酮类固醇和前列腺素D（2））显示出广泛的底物特异性，它们被转化为3alpha-，17beta-和20alpha -羟基类固醇和9alpha，11beta-前列腺素F（2），分别。特别是，α-二酮（如isatin和diacetyl）和脂质过氧化衍生的醛（如4-oxo-和4-hydroxy-2-nonenals）是显示低K（m）值（0
• Reactive Carbonyl-Scavenging Ability of 2-Aminoimidazoles: 2-Amino-1-methylbenzimidazole and 2-Amino-1-methyl-6-phenylimidazo[4,5-<i>b</i>]pyridine (PhIP)
  作者：Francisco J. Hidalgo、Esmeralda Alcón、Rosario Zamora

  DOI：10.1021/jf504320a

  日期：2014.12.10

  The carbonyl-scavenging ability of 2-amino-1-methylbenzimidazole (AMBI) and the heterocyclic aromatic amine 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) was investigated in an attempt to identify new routes that can modify the carbonyl content of foods. The reaction of both AMBI and PhIP with 2-alkenals, 2,4-alkadienals, 4-oxo-2-alkenals, 4,5-epoxy-2-alkenals, and 4-hydroxy-2-nonenal produced

  为了鉴定2-氨基-1-甲基苯并咪唑（AMBI）和杂环芳香胺2-氨基-1-甲基-6-苯基咪唑并[4,5- b ]吡啶（PhIP）的羰基清除能力，可以改变食品中羰基含量的新途径。AMBI和PhIP与2-烯醛，2,4-链二烯醛，4-氧代-2-烯醛，4,5-环氧-2-烯醛和4-羟基-2-壬烯的反应生成了荧光加合物，其结构确定了AMBI和2-戊烯之间产生的加合物。分离并通过一维和二维核磁共振和高分辨率质谱鉴定该加合物为2,10-二氢-2-乙基-10-甲基嘧啶[1,2- a ]苯并咪唑。这些加合物的形成与消除AMBI和PhIP平行。这PhIP与4-氧代-2-壬烯醛之间的反应E a为27.4kJ / mol。所有这些结果表明2-氨基咪唑可用于改变食品的羰基含量。同时，由于该反应使氨基化合物消失，因此可以使用脂质衍生的羰基化合物消除2-氨基咪唑，这为消除食品中的杂环芳香胺提供了新的策略。
• Characterization of 2‘-Deoxyadenosine Adducts Derived from 4-Oxo-2-nonenal, a Novel Product of Lipid Peroxidation
  作者：Seon Hwa Lee、Diane Rindgen、Roy H. Bible,、Elisabeth Hajdu、Ian A. Blair

  DOI：10.1021/tx000057z

  日期：2000.7.1

  exocyclic amino group (N(6)) of 2'-deoxyadenosine was attached to C-1 of the 4-oxo-2-nonenal. The reaction of 4-oxo-2-nonenal with calf thymus DNA was also shown to result in the formation of substituted ethano adducts A(1) and A(2) and substituted etheno adduct B. Adduct B was formed in amounts almost 2 orders of magnitude greater than those of adducts A(1) and A(2). This was in keeping with the observed

  通过液相色谱/质谱法分析2'-脱氧腺苷与4-氧代-2-壬烯醛之间的反应，发现存在三种主要产物（加合物A（1），A（2）和B）。加合物A（1）和A（2）是异构体；它们在室温下相互转化，并且每个都容易脱水形成加合物B。通过碰撞诱导解离与多串联质谱联用获得的加合物B的质谱特征与取代的乙炔加合物所预期的一致。NMR光谱显示加合物B的结构与取代的乙炔-2'-脱氧腺苷加合物1''-[3-（2'-脱氧-β-D-赤藓型呋喃呋喃糖基）-3H-咪唑并[2，1 -i]嘌呤-7-基]庚烷-2'-一。结构的明确证据来自加合物A（1）和A（2）（加合物B的前体）与硼氢化钠的反应。加合物A（1）和A（2）各自形成相同的还原产物，其中包含八个额外的氢原子。该还原产物的质谱特性确定了2'-脱氧腺苷的环外氨基（N（6））连接到4-氧代-2-壬烯醛的C-1。还显示了4-氧代-2-壬烯醛与小牛胸腺DNA的反应导致形成取代的乙醇加