β-D-glucopyranose 1-[(E)-3-(3,4-dihydroxyphenyl)-2-propenoate] | 13080-40-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: β-D-glucopyranose 1-[(E)-3-(3,4-dihydroxyphenyl)-2-propenoate]
• 英文别名: 1-O-[(E)-caffeoyl]-β-D-glucopyranose；1-O-(E)-caffeoyl-β-D-glucopyranose；1-O-E-caffeoyl β-D-glucopyranose；1-O-caffeoyl β-D-glucopyranoside；1-O-caffeoyl-β-D-glucopyranoside；1-O-caffeoyl-β-D-glucopyranose；1-Caffeoyl-beta-D-glucose；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 13080-40-5
• 化学式: C₁₅H₁₈O₉
• 分子量: 342.303
• InChiKey: WQSDYZZEIBAPIN-VBQORRLJSA-N

物化性质

• 沸点：
  644.7±55.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  β-D-glucopyranose 1-[(E)-3-(3,4-dihydroxyphenyl)-2-propenoate] 生成 D-葡萄糖
  参考文献：
  名称：

  KURKIN, V. A.;ZAPESOCHNAYA, G. G.;NIKOLAJCHUK, V. I.;BELCHGAZI, V. I., XIMIYA PRIROD. SOED.,(1989) N, S. 851-852

  摘要：

  DOI：
• 作为产物：
  描述：

  在 palladium on activated charcoal 1,4-环己二烯 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以40%的产率得到β-D-glucopyranose 1-[(E)-3-(3,4-dihydroxyphenyl)-2-propenoate]
  参考文献：
  名称：

  Chemical Synthesis of Hydroxycinnamic Acid Glucosides and Evaluation of Their Ability To Stabilize Natural Colors via Anthocyanin Copigmentation

  摘要：

  This work describes the chemical synthesis of O-aryi-beta-D-glucosides and 1 -O-beta-D-glucosyl esters of hydroxycinnamic acids. In particular, OLaryl-beta-D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O-beta-D-caffeoylglucose could also be obtained using a Lewis acid catalyzed glycosylation step and a set of protective groups that can be removed under neutral conditions. Hydroxycinnamic acid O-aryl-beta-D-glucosides were then quantitatively investigated for their affinity for the naturally occurring anthocyanin malvin (pigment). Formation of the pi-stacking molecular complexes (copigmentation) was characterized in terms of binding constants and enthalpy and entropy changes. The glucosyl moiety did not significantly alter these thermodynamic parameters, in line with a binding process solely involving the polyphenolic nuclei.

  DOI：

  10.1021/jf071205v

文献信息

• Engineering faster transglycosidases and their acceptor specificity
  作者：Linh T. Tran、Vincent Blay、Sukanya Luang、Chatchakorn Eurtivong、Sunaree Choknud、Humbert González-Díaz、James R. Ketudat Cairns

  DOI：10.1039/c9gc00621d

  日期：——

  L241D/W243N. In order to guide a more general use of Os9BGlu31 variants as transglycosylation catalysts, we built cheminformatics models based on topological descriptors of the substrates. These models showed useful predictive potential on the external validation set and are allowing the identification of efficient catalytic routes to novel phytohormone and antibiotic glucoconjugates of interest.

  转糖苷酶是具有催化从生物质衍生的原料开始的各种高价值化合物合成的酶。改善其活性并拓宽底物范围是使该生物催化剂家族广泛应用的重要目标。在这项工作中，我们设计了20个水稻转糖苷酶Os9BGlu31突变体，并评估了它们在18种不同底物上的462次反应中的催化作用。这使我们能够鉴定出扩大了其底物范围并显示出高活性的突变体，包括W243L和W243N。我们还开发了双重突变体，例如L241D / W243N，它们在某些底物上具有很高的活性，并且对水解具有特殊的特异性。为了指导Os9BGlu31变体更普遍地用作转糖基化催化剂，我们基于底物的拓扑描述符建立了化学信息学模型。这些模型在外部验证集上显示出有用的预测潜力，并且允许鉴定出有效的催化途径，以催化新型目标植物激素和抗生素葡萄糖缀合物。
• Identification of Glucosyltransferase Genes Involved in Sinapate Metabolism and Lignin Synthesis in Arabidopsis
  作者：Eng-Kiat Lim、Yi Li、Adrian Parr、Ros Jackson、David A. Ashford、Dianna J. Bowles

  DOI：10.1074/jbc.m007263200

  日期：2001.2

  identified. Combining sequence information in the Arabidopsis genomic data base with biochemical data from screening the activity of recombinant proteins in vitro, we have now identified five gene sequences encoding enzymes that can glucosylate sinapic acid, sinapyl alcohol, and their related phenylpropanoids. The data provide a foundation for future understanding and manipulation of sinapate metabolism

  芥子酸是十字花科中的主要苯基丙烷，在两个不同的代谢途径中提供中间体，从而导致芥子酸酯和木质素合成。葡萄糖基转移酶在这些中间体的形成中起关键作用，通过产生高能化合物1-O-芥子酰葡萄糖导致芥子酸苹果酸酯和芥子碱胆碱，或通过产生芥子醇-4-O-葡糖苷，可能导致丁香基单元在木质素中发现。尽管已经认识了这些葡糖基转移酶的重要性超过20年，但尚未鉴定出它们的相应基因。将拟南芥基因组数据库中的序列信息与通过体外筛选重组蛋白活性而获得的生化数据相结合，我们现在已经确定了五个编码酶的基因序列，这些酶可以使芥子酸，芥子醇及其相关的苯基丙烷类糖基化。这些数据为将来了解和操纵拟南芥中的芥子酸酯代谢和木质素生物学奠定了基础。
• NOVEL AROMATIC ACYL GROUP TRANSFERASE GENE
  申请人：Aomori prefecture

  公开号：EP1947179A1

  公开（公告）日：2008-07-23

  The present invention provides a protein having the amino acid sequence as shown in SEQ ID NO: 2, 4, 6, 8, 10 or 12 or a protein having a modified amino acid sequence thereof and having an activity of transferring an aromatic acyl group to a sugar residue of a flavonoid; a gene, especially cDNA, encoding the protein; and use thereof For example, by introducing the above gene into a plant expressing hydroxycinnamate 1-O-glucosyltransferase gene, optionally together with a cDNA encoding a protein having the amino acid sequence as shown in SEQ ID NO: 14, 16 or 18 or a protein having an amino acid sequence derived therefrom by modification and having an activity of glucosylating a hydroxyl group at position 1 of hydroxycinnamic acid, and then expressing the introduced gene(s), it is possible to acylate the sugar residue of flavonoids in flowers of the plant to thereby confer a blue color on the flowers.

  本发明提供了一种具有 SEQ ID NO：2、4、6、8、10 或 12 所示氨基酸序列的蛋白质，或其氨基酸序列经修饰并具有将芳香酰基转移到类黄酮的糖残基上的活性的蛋白质；编码该蛋白质的基因，特别是 cDNA；及其用途 例如，将上述基因导入表达羟基肉桂酸 1-O-葡萄糖基转移酶基因的植物中，任选与编码具有 SEQ ID NO：14、16 或 18 所示氨基酸序列的蛋白质，或其氨基酸序列经修饰后得到的具有羟基肉桂酸 1 位羟基葡萄糖基化活性的蛋白质，然后表达导入的基因，就可以使植物花朵中黄酮类化合物的糖残基酰化，从而使花朵呈现蓝色。
• NOVEL GLYCOSYLTRANSFERASE, NOVEL GLYCOSYLTRANSFERASE GENE, AND NOVEL GLYCOSYL DONOR COMPOUND
  申请人：National University Corporation Tokyo University Of Agriculture and Technology

  公开号：EP2463366B1

  公开（公告）日：2015-08-12
• KURKIN, V. A.;ZAPESOCHNAYA, G. G.;NIKOLAJCHUK, V. I.;BELCHGAZI, V. I., XIMIYA PRIROD. SOED.,(1989) N, S. 851-852
  作者：KURKIN, V. A.、ZAPESOCHNAYA, G. G.、NIKOLAJCHUK, V. I.、BELCHGAZI, V. I.

  DOI：——

  日期：——