guaiacylglycerol-β-O-4′-coniferyl alcohol | 1103-58-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: guaiacylglycerol-β-O-4′-coniferyl alcohol
• 英文别名: (+/-)-guaiacylglycerin-8-O-4'-coniferyl ether；Guajacylglycerin-β-coniferylether；Guajacyl-glycerin-β-coniferylether；1-(4-Hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxyprop-1-enyl)-2-methoxyphenoxy]propane-1,3-diol
• CAS: 1103-58-8
• 化学式: C₂₀H₂₄O₇
• 分子量: 376.406
• InChiKey: FYEZJIXULOZDRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  松柏醇 在 Trametes versicolor laccase 、 双氧水 作用下， 生成 guaiacylglycerol-β-O-4′-coniferyl alcohol 、 松脂酚 、 (±)-dehydrodiconiferyl alcohol
  参考文献：
  名称：

  Hitherto Unrecognized Fluorescence Properties of Coniferyl Alcohol

  摘要：

  我们制定了准质量保证计划，用于证明松柏醇的荧光和酶氧化后的荧光减弱。减少的幅度是催化作用的衡量标准。通过在 290、310 或 340 nm 激发后测量 416 nm 处的荧光，以伪动力学和终点模式进行高通量筛选。剂量反应追踪在两个和三个数量级之间呈线性，平均检测限和定量限分别为 1.8 和 6.9 mM 松柏醇。使用 0.025 mg/mL 漆酶或 0.003 mg/mL 过氧化物酶或使用 0.5 mg/mL 漆酶或 5 mM 底物在 5 分钟内氧化明显。氯化钠抑制（IC50，25 mM）松柏醇漆酶氧化。 10 个浓度（1 至 1000 mM）的松柏醇的荧光在 3 种不同的激发和发射波长组合下的 14 个激发/发射循环中可稳定保持 24 小时。总之，松柏醇吸收和荧光测定应有助于生物质木质素分析并改善脱木质素。

  DOI：

  10.3390/molecules15031645

文献信息

• The synthesis and analysis of advanced lignin model polymers
  作者：C. S. Lancefield、N. J. Westwood

  DOI：10.1039/c5gc01334h

  日期：——

  Advanced lignin model polymers have been synthesised to aid in the development of new methods for lignin valorisation.

  高级木质素模型聚合物已经合成，以帮助开发木质素增值的新方法。
• Incorporation of catechyl monomers into lignins: lignification from the non-phenolic end <i>via</i> Diels–Alder cycloaddition?
  作者：Daisuke Ando、Fachuang Lu、Hoon Kim、Alexis Eugene、Yuki Tobimatsu、Ruben Vanholme、Thomas J. Elder、Wout Boerjan、John Ralph

  DOI：10.1039/d1gc03022a

  日期：——

  diene in a hetero-Diels–Alder reaction, a benzodioxane structure was produced with a different regiochemistry than the benzodioxane isomer produced via radical coupling; (ii) when the quinone's diene participated in the Diels–Alder reaction, a distinctive oxatricyclo structure was produced. Both features may be used as markers for the occurrence of Diels–Alder reactions in lignification. Examination

  典型的木质化通过酚自由基的偶联发生，其中链延伸只能从增长的聚合物链的酚末端发生。儿茶基单体（包括咖啡醇和 5-羟基松柏醇）的自由基偶联会在聚合物中产生苯并二恶烷单元。预计邻苯二酚可以在木质化的脱氢（氧化）条件下氧化为其邻苯醌类似物，我们研究了邻苯醌作为二烯组分也可以通过另一种机制 Diels-Alder并入木质素的可能性环加成反应。5-羟基香草酸甲酯和4- O衍生的邻苯醌-甲基松柏醇分别作为二烯和亲二烯体的模型，并在体外产生 Diels-Alder 产物。发现了两种类型的 Diels-Alder 产物：(i) 当醌的 1,2-二酮在杂 Diels-Alder 反应中充当二烯时，产生的苯二恶烷结构与所产生的苯二恶烷异构体具有不同的区域化学通过自由基耦合；(ii) 当醌的二烯参与 Diels-Alder 反应时，产生了独特的氧杂环结构。这两个特征都可以用作木质化过程中 Diels-Alder
• An Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols
  作者：Benjamin Pickel、Mihaela-Anca Constantin、Jens Pfannstiel、Jürgen Conrad、Uwe Beifuss、Andreas Schaller

  DOI：10.1002/anie.200904622

  日期：2010.1.4

  formed during laccase‐catalyzed phenol coupling of (E)‐coniferyl alcohol (1) depends on the dirigent protein. In the presence of the first enantiocomplementary dirigent protein AtDIR6, (−)‐2 is formed (78 % ee). Preferential formation of (+)‐2 is observed in the presence of the dirigent protein FiDIR1, whereas only racemic 2 is formed in the absence of dirigent proteins.

  （+）-或（-）-松脂醇：这是问题。这两种对映体木脂素中的哪一种是在（E）-松柏醇（1）的漆酶催化的苯酚偶联过程中形成的，这取决于不同的蛋白质。在第一enantiocomplementary dirigent蛋白的存在在DIR6，（ - ） - 2形成（78％  EE）。在存在差异蛋白Fi DIR1的情况下观察到（+）- 2的优先形成，而在不存在差异蛋白的情况下仅形成外消旋2。
• On the reactivity of the Melanocarpus albomyces laccase and formation of coniferyl alcohol dehydropolymer (DHP) in the presence of ionic liquid 1-allyl-3-methylimidazolium chloride
  作者：Maarit Lahtinen、Liisa Viikari、Pirkko Karhunen、Janne Asikkala、Kristiina Kruus、Ilkka Kilpeläinen

  DOI：10.1016/j.molcatb.2012.09.005

  日期：2013.1

  Some ionic liquids are able to dissolve wood, including lignin and lignocellulose, and thus they provide an efficient reaction media for modification of globally abundant wood-based polymers. Lignin can be modified with laccases (EC 1.10.3.2), multicopper oxidases, which selectively catalyze the oxidation of phenolic hydroxyl to the phenoxy radical in lignin by using oxygen as the co-substrate and an electron acceptor. Many enzymes, including laccases, retain their catalytic activity in the presence of ionic liquids. However, the enzyme activity is usually decreased in the presence of ionic liquids, and the most deactivating ionic liquids have been observed to be those dissolving wood most efficiently. In the present study the activity, pH optimum and catalyzed oxidation of coniferyl alcohol by the laccase from the ascomycete Melanocarpus albomyces was investigated in the ionic liquid 1-allyl-3-methyl-imidazolium chloride ([Amim]Cl), known to dissolve wood and expected to affect the laccase activity. Indeed, with an increasing concentration of [Amim]Cl, the activity of M. albomyces laccase decreased, and the pH range of the enzyme activity was narrowed. The pH optimum, using 2,6-dimethoxyphenol as the substrate, was shifted from 6.5 to 6.0 when the amount of [Amim]Cl was increased to 60% (m-%). It was also found that the inhibition of laccase with NaN3 was not as severe in the ionic liquid as in water. The insoluble fraction of the dehydropolymer (DHP) formed in the presence of [Amim]Cl had clearly higher molecular weight compared to the one formed in water. DHPs formed in the absence and presence of [Amim]Cl both contained beta-5, beta-beta, beta-O-4, alpha-C=O/beta-O-4 and alpha-O-4/beta-O-4 structures. However, in the presence of [Amim]Cl, less beta-O-4, slightly less beta-5 and more beta-beta structures were formed. (C) 2012 Elsevier B.V. All rights reserved.
• Hitherto Unrecognized Fluorescence Properties of Coniferyl Alcohol
  作者：Komandoor Elayavalli Achyuthan、Paul David Adams、Supratim Datta、Blake Alexander Simmons、Anup Kumar Singh

  DOI：10.3390/molecules15031645

  日期：——

  We instituted a quasi-quality assurance program for demonstrating coniferyl alcohol’s fluorescence and fluorescence diminishment following enzymatic oxidation. The magnitude of diminishment was a measure of catalysis. High throughput screening was performed in pseudo-kinetic and endpoint modes by measuring the fluorescence at 416 nm following excitation at 290, 310 or 340 nm. Dose-response tracings were linear between two and three orders of magnitude with average limits of detection and quantitation of 1.8 and 6.9 mM coniferyl alcohol, respectively. Oxidation was evident with 0.025 mg/mL laccase or 0.003 mg/mL peroxidase or inside 5 min using 0.5 mg/mL laccase or 5 mM substrate. Sodium chloride inhibited (IC50, 25 mM) laccase oxidation of coniferyl alcohol. Fluorescence from 10 concentrations (1 to 1000 mM) of coniferyl alcohol was stable for 24 hours over 14 excitation/emission cycles at 3 different combinations of excitation and emission wavelengths. In conclusion, coniferyl alcohol absorption and fluorescence assays should facilitate biomass lignin analyses and improve delignification.

  我们制定了准质量保证计划，用于证明松柏醇的荧光和酶氧化后的荧光减弱。减少的幅度是催化作用的衡量标准。通过在 290、310 或 340 nm 激发后测量 416 nm 处的荧光，以伪动力学和终点模式进行高通量筛选。剂量反应追踪在两个和三个数量级之间呈线性，平均检测限和定量限分别为 1.8 和 6.9 mM 松柏醇。使用 0.025 mg/mL 漆酶或 0.003 mg/mL 过氧化物酶或使用 0.5 mg/mL 漆酶或 5 mM 底物在 5 分钟内氧化明显。氯化钠抑制（IC50，25 mM）松柏醇漆酶氧化。 10 个浓度（1 至 1000 mM）的松柏醇的荧光在 3 种不同的激发和发射波长组合下的 14 个激发/发射循环中可稳定保持 24 小时。总之，松柏醇吸收和荧光测定应有助于生物质木质素分析并改善脱木质素。