5-hydroxyconiferyl aldehyde | 249647-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-hydroxyconiferyl aldehyde
• 英文别名: 5-hydroxyconiferaldehyde；coniferaldehyde；4,5-Dihydroxy-3-methoxycinnamaldehyde；3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enal
• CAS: 249647-14-1
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: IEHPLRVWOHZKCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxyconiferyl aldehyde 在 Plagiochasma appendiculatum alkenal double bond reductase 2 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.5h， 生成 dihydro-5-hydroxyconiferyl aldehyde
  参考文献：
  名称：

  A single amino acid determines the catalytic efficiency of two alkenal double bond reductases produced by the liverwortPlagiochasma appendiculatum

  摘要：

  Alkenal double bond reductases (DBRs) catalyze the NADPH‐dependent reduction of the α,β‐unsaturated double bond of many secondary metabolites. Two alkenal double bond reductase genes PaDBR1 and PaDBR2 were isolated from the liverwort species Plagiochasma appendiculatum. Recombinant PaDBR2 protein had a higher catalytic activity than PaDBR1 with respect to the reduction of the double bond present in hydroxycinnamyl aldehydes. The residue at position 56 appeared to be responsible for this difference in enzyme activity. The functionality of a C56 to Y56 mutation in PaDBR1 was similar to that of PaDBR2. Further site‐directed mutagenesis and structural modeling suggested that the phenol ring stacking between this residue and the substrate was an important determinant of catalytic efficiency.

  DOI：

  10.1016/j.febslet.2013.07.051
• 作为产物：
  描述：

  5-Hydroxyeugenol 在 碳酸氢钠 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 17.0h， 生成 5-hydroxyconiferyl aldehyde
  参考文献：
  名称：

  一种4-羟基肉桂醛类化合物的合成方法

  摘要：

  本发明申请涉及有机合成与农业化学领域，具体公开了一种合成式II所示4‑羟基肉桂醛类化合物的合成方法，该方法以4‑羟基烯丙基苯为原料，首先进行羟基保护，然后利用2,3‑二氯‑5,6‑二氰基‑1,4‑苯醌(DDQ)为氧化剂，水(H2O)为亲核试剂，在较温和条件下氧化烯丙基为α,β‑不饱和醛(即肉桂醛结构)，最后脱保护得到目标产物。本发明阐述了一种4‑羟基肉桂醛类化合物的合成新方法，具有无过渡金属的参与，反应条件简单温和，产物收率高等特点，在农业化学特别是植物科学和生物能源转化领域有广泛的应用前景。

  公开号：

  CN107573226A

文献信息

• Insights into lignin primary structure and deconstruction from Arabidopsis thaliana COMT (caffeic acid O-methyl transferase) mutant Atomt1
  作者：Syed G. A. Moinuddin、Michaël Jourdes、Dhrubojyoti D. Laskar、Chanyoung Ki、Claudia L. Cardenas、Kye-Won Kim、Dianzhong Zhang、Laurence B. Davin、Norman G. Lewis

  DOI：10.1039/c004817h

  日期：——

  The Arabidopsis mutant Atomt1 lignin differs from native lignin in wild type plants, in terms of sinapyl (S) alcohol-derived substructures in fiber cell walls being substituted by 5-hydroxyconiferyl alcohol (5OHG)-derived moieties. During programmed lignin assembly, these engender formation of benzodioxane substructures due to intramolecular cyclization of their quinone methides that are transiently formed following 8-O-4′ radical-radical coupling. Thioacidolytic cleavage of the 8-O-4′ inter-unit linkages in the Atomt1 mutant, relative to the wild type, indicated that cleavable sinapyl (S) and coniferyl (G) alcohol-derived monomeric moieties were stoichiometrically reduced by a circa 2 : 1 ratio. Additionally, lignin degradative analysis resulted in release of a 5OHG–5OHG–G trimer from the Atomt1 mutant, which then underwent further cleavage. Significantly, the trimeric moiety released provides new insight into lignin primary structure: during polymer assembly, the first 5OHG moiety is linked via a C8–O–X inter-unit linkage, whereas subsequent addition of monomers apparently involves sequential addition of 5OHG and G moieties to the growing chain in a 2 : 1 overall stoichiometry. This quantification data thus provides further insight into how inter-unit linkage frequencies in native lignins are apparently conserved (or near conserved) during assembly in both instances, as well as providing additional impetus to resolve how the overall question of lignin macromolecular assembly is controlled in terms of both type of monomer addition and primary sequence.

  拟南芥突变体 Atomt1 木质素与野生型植物中的原生木质素不同，纤维细胞壁中由 sinapyl (S) 醇衍生的亚结构被 5-hydroxyconiferyl 醇 (5OHG) 衍生的分子取代。在木质素的程序化组装过程中，由于 8-O-4′ 自由基-自由基偶联后瞬时形成的醌基甲烷的分子内环化作用，这些醌基甲烷会形成苯并二恶烷亚结构。与野生型相比，Atomt1 突变体中 8-O-4′ 单元间连接的硫代酸裂解表明，可裂解的桧醇（S）和松柏醇（G）衍生的单体分子以约 2 ：1 的比例减少。此外，木质素降解分析还导致 Atomt1 突变体释放出 5OHG-5OHG-G 三聚体，然后进一步裂解。值得注意的是，释放出的三聚体提供了对木质素一级结构的新认识：在聚合物组装过程中，第一个 5OHG 分子通过 C8-O-X 单元间连接，而随后单体的添加显然涉及 5OHG 和 G 分子以 2 ：1 的总比例。因此，这些定量数据让我们进一步了解了在这两种情况下，原生木质素中的单元间连接频率是如何在组装过程中保持不变（或接近不变）的，同时也为解决木质素大分子组装的整体问题提供了更多动力，即单体添加类型和主序是如何受控的。
• A single amino acid determines the catalytic efficiency of two alkenal double bond reductases produced by the liverwort<i>Plagiochasma appendiculatum</i>
  作者：Yifeng Wu、Yuanheng Cai、Yi Sun、Ruixue Xu、Haina Yu、Xiaojuan Han、Hongxiang Lou、Aixia Cheng

  DOI：10.1016/j.febslet.2013.07.051

  日期：2013.9.17

  Alkenal double bond reductases (DBRs) catalyze the NADPH‐dependent reduction of the α,β‐unsaturated double bond of many secondary metabolites. Two alkenal double bond reductase genes PaDBR1 and PaDBR2 were isolated from the liverwort species Plagiochasma appendiculatum. Recombinant PaDBR2 protein had a higher catalytic activity than PaDBR1 with respect to the reduction of the double bond present in hydroxycinnamyl aldehydes. The residue at position 56 appeared to be responsible for this difference in enzyme activity. The functionality of a C56 to Y56 mutation in PaDBR1 was similar to that of PaDBR2. Further site‐directed mutagenesis and structural modeling suggested that the phenol ring stacking between this residue and the substrate was an important determinant of catalytic efficiency.
• 一种4-羟基肉桂醛类化合物的合成方法
  申请人：安徽农业大学

  公开号：CN107573226A

  公开（公告）日：2018-01-12

  本发明申请涉及有机合成与农业化学领域，具体公开了一种合成式II所示4‑羟基肉桂醛类化合物的合成方法，该方法以4‑羟基烯丙基苯为原料，首先进行羟基保护，然后利用2,3‑二氯‑5,6‑二氰基‑1,4‑苯醌(DDQ)为氧化剂，水(H2O)为亲核试剂，在较温和条件下氧化烯丙基为α,β‑不饱和醛(即肉桂醛结构)，最后脱保护得到目标产物。本发明阐述了一种4‑羟基肉桂醛类化合物的合成新方法，具有无过渡金属的参与，反应条件简单温和，产物收率高等特点，在农业化学特别是植物科学和生物能源转化领域有广泛的应用前景。