vanillic acid 1-O-B-glucopyranosyl ester | 68985-14-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: vanillic acid 1-O-B-glucopyranosyl ester
• 英文别名: 1-O-vanilloyl-β-D-glucose；vanillic acid glucosyl ester；1-O-vanilloyl-beta-D-glucose；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 4-hydroxy-3-methoxybenzoate
• CAS: 68985-14-8
• 化学式: C₁₄H₁₈O₉
• 分子量: 330.292
• InChiKey: YROOZUQRTLHXIO-DIACKHNESA-N

物化性质

• 熔点：
  224 °C
• 沸点：
  595.9±50.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  cyanidin-3-glucoside 、 vanillic acid 1-O-B-glucopyranosyl ester 在 柠檬酸 作用下， 反应 3.0h， 生成 cyanidin-3,7-β-O-diglucoside
  参考文献：
  名称：

  NOVEL GLYCOSYLTRANSFERASE, NOVEL GLYCOSYLTRANSFERASE GENE, AND NOVEL GLYCOSYL DONOR COMPOUND

  摘要：

  公开号：

  EP2463366B1
• 作为产物：
  描述：

  4-(benzoyloxy)benzoyl chloride 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 反应 93.0h， 生成 vanillic acid 1-O-B-glucopyranosyl ester
  参考文献：
  名称：

  植物中羟基苯甲酸的葡萄糖苷和葡萄糖酯

  摘要：

  摘要 合成了6种羟基苯甲酸葡萄糖苷和3种羟基苯甲酰葡萄糖作为对照品，采用毛细管气相色谱和高效液相色谱法测定植物提取物中的含量。结果表明糖苷分布广泛，而葡萄糖酯的出现频率较低。

  DOI：

  10.1016/0031-9422(88)80121-3

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 UGT84A13 as a candidate enzyme for the first committed step of gallotannin biosynthesis in pedunculate oak (Quercus robur)
  作者：Juliane Mittasch、Christoph Böttcher、Nadezhda Frolova、Markus Bönn、Carsten Milkowski

  DOI：10.1016/j.phytochem.2013.11.023

  日期：2014.3

  UDP-glucose:gallic acid glucosyltransferase activity. UGT84A13 was functionally expressed in Escherichia coli as N-terminal His-tagged protein. In vitro kinetic measurements with the purified recombinant enzyme revealed a clear preference for hydroxybenzoic acids as glucosyl acceptor in comparison to hydroxycinnamic acids. Of the preferred in vitro substrates, protocatechuic, vanillic and gallic acid, only

  编码形成酯的羟基苯甲酸葡萄糖基转移酶 UGT84A13 的 cDNA 是从 Quercus robur 膨胀芽和幼叶的 cDNA 文库中分离出来的。该酶与来自葡萄属的白藜芦醇/羟基肉桂酸酯和羟基苯甲酸酯/羟基肉桂酸酯葡萄糖基转移酶显示出高度的序列同一性，并聚集在植物葡萄糖基转移酶的系统发育组 L 中，主要参与 1-O-β-D-葡萄糖酯的形成。计算机转录组分析证实了 UGT84A13 在 Quercus 组织中的表达，该组织之前显示出 UDP-葡萄糖：没食子酸葡萄糖基转移酶活性。UGT84A13 在大肠杆菌中作为 N 端 His 标记蛋白在功能上表达。用纯化的重组酶进行的体外动力学测量显示，与羟基肉桂酸相比，羟基苯甲酸明显更倾向于作为葡萄糖基受体。在优选的体外底物原儿茶酸、香草酸和没食子酸中，只有后者及其相应的 1-O-β-D-葡萄糖酯被发现在年轻的橡树叶中积累。这表明在植物中 UGT84A13
• A Novel Glucosylation Reaction on Anthocyanins Catalyzed by Acyl-Glucose–Dependent Glucosyltransferase in the Petals of Carnation and Delphinium  
  作者：Yuki Matsuba、Nobuhiro Sasaki、Masayuki Tera、Masachika Okamura、Yutaka Abe、Emi Okamoto、Haruka Nakamura、Hisakage Funabashi、Makoto Takatsu、Mikako Saito、Hideaki Matsuoka、Kazuo Nagasawa、Yoshihiro Ozeki

  DOI：10.1105/tpc.110.077487

  日期：2010.11.24

  Glucosylation of anthocyanin in carnations (Dianthus caryophyllus) and delphiniums (Delphinium grandiflorum) involves novel sugar donors, aromatic acyl-glucoses, in a reaction catalyzed by the enzymes acyl-glucose–dependent anthocyanin 5(7)-O-glucosyltransferase (AA5GT and AA7GT). The AA5GT enzyme was purified from carnation petals, and cDNAs encoding carnation Dc AA5GT and the delphinium homolog Dg AA7GT were isolated. Recombinant Dc AA5GT and Dg AA7GT proteins showed AA5GT and AA7GT activities in vitro. Although expression of Dc AA5GT in developing carnation petals was highest at early stages, AA5GT activity and anthocyanin accumulation continued to increase during later stages. Neither Dc AA5GT expression nor AA5GT activity was observed in the petals of mutant carnations; these petals accumulated anthocyanin lacking the glucosyl moiety at the 5 position. Transient expression of Dc AA5GT in petal cells of mutant carnations is expected to result in the transfer of a glucose moiety to the 5 position of anthocyanin. The amino acid sequences of Dc AA5GT and Dg AA7GT showed high similarity to glycoside hydrolase family 1 proteins, which typically act as β-glycosidases. A phylogenetic analysis of the amino acid sequences suggested that other plant species are likely to have similar acyl-glucose–dependent glucosyltransferases.

  石竹（Dianthus caryophyllus）和翠雀花（Delphinium grandiflorum）中花青素的葡萄糖化涉及新型糖基供体，芳香基酰基葡萄糖，由酰基葡萄糖依赖的花青素5（7）-O-葡萄糖基转移酶（AA5GT和AA7GT）催化反应。从石竹花瓣中纯化了AA5GT酶，并分离了编码石竹Dc AA5GT和翠雀花同源物Dg AA7GT的cDNA。重组的Dc AA5GT和Dg AA7GT蛋白在体外表现出AA5GT和AA7GT活性。虽然Dc AA5GT在石竹花瓣的发育早期表达最高，但AA5GT活性和花青素积累在后期仍然持续增加。在突变石竹花瓣中，既没有观察到Dc AA5GT表达，也没有AA5GT活性；这些花瓣积累了缺乏5位葡萄糖基的花青素。预计在突变石竹花瓣细胞中短暂表达Dc AA5GT将导致将葡萄糖基转移至花青素的5位。Dc AA5GT和Dg AA7GT的氨基酸序列与糖苷水解酶家族1蛋白的高度相似，这些蛋白通常作为β-葡萄糖苷酶。氨基酸序列的系统发育分析表明，其他植物物种可能具有类似的酰基葡萄糖依赖性葡萄糖转移酶。

• Enzymatic synthesis of phenolic acid glucosyl esters to test activities on cholangiocarcinoma cells
  作者：Eko Suyanto、Jaggaiah N. Gorantla、Maniganda Santi、Fatchiyah Fatchiyah、Mariena Ketudat-Cairns、Chutima Talabnin、James R. Ketudat Cairns

  DOI：10.1007/s00253-023-12895-5

  日期：2024.12

  anti-proliferative assays, followed by an anti-migration assay for the selected phenolic acid glucosyl ester. Os9BGlu31 mutants produced higher yield and activity than wild-type enzymes on phenolic acids to produce phenolic acid glucosyl esters. Among these, gallic acid glucosyl ester (β-glucogallin) had the highest antioxidant activity and anti-proliferative activity in cholangiocarcinoma cells. It also inhibited

  糖苷水解酶家族 1 (GH1) 酶主要催化水解反应，而水稻 Os9BGlu31 优先催化转糖基化，将一个葡萄糖基部分转移到另一个糖苷配基部分，通过保留机制形成新的糖基化化合物。在本研究中，Os9BGlu31 用于合成八种酚酸葡萄糖酯，并评估其在胆管癌细胞中的活性。对Os9BGlu31野生型及其突变体的转糖基化产物进行了检测、毫克级生产和纯化，并通过核磁共振波谱表征了它们的结构。通过抗氧化剂和抗增殖测定评估转糖基化产物，然后对选定的酚酸葡萄糖酯进行抗迁移测定。 Os9BGlu31 突变体比野生型酶对酚酸产生更高的产量和活性，以产生酚酸葡萄糖酯。其中，没食子酸葡萄糖酯（β-glucogallin）在胆管癌细胞中具有最高的抗氧化活性和抗增殖活性。它还抑制胆管癌细胞的迁移。我们的研究表明，水稻 Os9BGlu31 转葡萄糖苷酶是一种有前景的一步反应中生物活性化合物糖基化酶，并提供了 β-葡萄糖没食
• Klamath Russet: A Full Season, Fresh Market, Long Russet
  作者：A. R. Mosley、K. A. Rykbost、S. R. James、D. C. Hane、C. C. Shock、B. A. Charlton、J. J. Pavek、S. L. Love、D. L. Corsini、R. E. Thornton

  DOI：10.1007/bf02884347

  日期：2001.9

  Klamath Russet, a late-maturing cultivar for fresh market use, was jointly released by the Agricultural Experiment Stations of Oregon, Idaho, and Washington and the U.S. Department of Agriculture in 2000. Klamath Russet was tested in irrigated trials in Oregon from 1990 to 1999 and in Western Regional Trials from 1994 to 1996. Klamath Russet yields of U.S. #1s have exceeded those for Russet Burbank and Russet Norkotah by more than 30%, averaged across all trials. Klamath Russet is moderately resistant to Verticillium wilt and highly resistant to common scab. Specific gravity for Klamath Russet has averaged 1.076 across all trials compared with 1.070 and 1.081 for Russet Norkotah and Russet Burbank, respectively. Klamath Russet is not considered suitable for french fry production because of high sugar and low starch contents.