1(E),2(E)-di-O-sinapoyl β-D-glucopyranoside | 91095-79-3

• 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: 1(E),2(E)-di-O-sinapoyl β-D-glucopyranoside
• 英文别名: 1(E),2(E)-di-O-sinapoyl-β-D-glucopyranoside；1,2-di-O-(E)-sinapoyl-β-glucopyranose；1,2-disinapoyl-β-D-glucopyranoside；1,2-di-O-sinapoyl-β-glucose；1,2-di-O-sinapoyl-beta-D-glucose；[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• CAS: 91095-79-3
• 化学式: C₂₈H₃₂O₁₄
• 分子量: 592.554
• InChiKey: KQDOTXAUJBODDM-STUNQXDBSA-N

物化性质

• 沸点：
  803.5±65.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  200
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1-sinapoyl-β-D-glucopyranoside 在 1-O-sinapoyl-β-glucose:L-malate sinapoyltransferase 作用下， 以 二甲基亚砜 为溶剂， 生成 3,5-二甲氧基-4-羟基肉桂酸 、 1(E),2(E)-di-O-sinapoyl β-D-glucopyranoside
  参考文献：
  名称：

  拟南芥 sinapoylglucose:malate sinapoyltransferase 的活性揭示丝氨酸羧肽酶样酰基转移酶的功能多样化

  摘要：

  对来自拟南芥的丝氨酸羧肽酶样 (SCPL) 1-O-sinapoyl-beta-glucose:l-malate sinapoyltransferase (SMT) 的催化特性的分析表明，该酶除了主要的 l-苹果酸sinapoylation 外，还具有少量水解和歧化活性，分别产生游离芥子酸和 1,2-二-O-芥子酰-β-葡萄糖。该酶从供体分子 1-O-sinapoyl-β-葡萄糖中释放芥子酸的能力表明在所提出的随机顺序双双催化机制中存在短寿命的酰基酶中间体。SMT 催化的 disinapoylglucose 形成已通过对接研究得到证实，已建立的同源结构模型说明了活性位点中两个 1-O-sinapoyl-β-葡萄糖分子的可能结合以及两种葡萄糖酯的分子间反应。SMT 基因嵌入五个 SCPL 芥子酰转移酶基因的串联簇中，这些基因编码具有高氨基酸序列同一性和部分重叠底物特异性的酶。我们假设在编码 SCPL

  DOI：

  10.1016/j.phytochem.2008.03.021

文献信息

• Related Arabidopsis Serine Carboxypeptidase-Like Sinapoylglucose Acyltransferases Display Distinct But Overlapping Substrate Specificities
  作者：Christopher M. Fraser、Michael G. Thompson、Amber M. Shirley、John Ralph、Jessica A. Schoenherr、Taksina Sinlapadech、Mark C. Hall、Clint Chapple

  DOI：10.1104/pp.107.098970

  日期：2007.8

  The Arabidopsis (Arabidopsis thaliana) genome encodes 51 proteins annotated as serine carboxypeptidase-like (SCPL) enzymes. Nineteen of these SCPL proteins are highly similar to one another, and represent a clade that appears to be unique to plants. Two of the most divergent proteins within this group have been characterized to date, sinapoyl-glucose (Glc):malate sinapoyltransferase and sinapoyl-Glc:choline sinapoyltransferase. The fact that two of the least related proteins within this clade are acyltransferases rather than true serine carboxypeptidases suggests that some or all of the remaining members of this group may have similar activities. The gene that encodes sinapoyl-Glc:malate sinapoyltransferase (sinapoyl-Glc accumulator1 [SNG1]: At2g22990) is one of five SCPL genes arranged in a cluster on chromosome 2. In this study, an analysis of deletion mutant lines lacking one or more genes in this SCPL gene cluster reveals that three of these genes also encode sinapoyl-Glc-dependent acyltransferases. At2g23000 encodes sinapoyl-Glc:anthocyanin acyltransferase, an enzyme that is required for the synthesis of the sinapoylated anthocyanins in Arabidopsis. At2g23010 encodes an enzyme capable of synthesizing 1,2-disinapoyl-Glc from two molecules of sinapoyl-Glc, an activity shared by SNG1 and At2g22980. Sequence analysis of these SCPL proteins reveals pairwise percent identities that range from 71% to 78%, suggesting that their differing specificities for acyl acceptor substrates are due to changes in a relatively small subset of amino acids. The study of these SCPL proteins provides an opportunity to examine enzyme structure-function relationships and may shed light on the role of evolution of hydroxycinnamate ester metabolism and the SCPL gene family in Arabidopsis and other flowering plants.

  酶。
• Probe compound for detecting and isolating enzymes and means and methods using the same
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2230312A1

  公开（公告）日：2010-09-22

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.

  本发明涉及一种探针化合物，它可以包括酶反应的任何底物或代谢物，此外还包括指示成分，例如荧光染料或类似物。此外，本发明还涉及以阵列形式检测酶的方法，该阵列由任意数量的本发明探针化合物组成，每种探针化合物由代表所有生命形式中中心途径的相互关联的代谢物中的不同代谢物组成。此外，本发明还涉及一种检测酶的方法，该方法涉及将细胞提取物或类似物应用于本发明的阵列，从而导致与底物发生可重复的酶反应。这些特定的酶反应会触发指示剂（如荧光信号），并将酶与各自的同源底物结合。此外，本发明还涉及以涂覆有本发明探针化合物的纳米颗粒形式分离酶的方法。通过探针化合物将同源底物或代谢物固定在纳米颗粒表面，可以捕获和分离相应的酶，例如用于后续测序。
• Activities of Arabidopsis sinapoylglucose:malate sinapoyltransferase shed light on functional diversification of serine carboxypeptidase-like acyltransferases
  作者：Felix Stehle、Wolfgang Brandt、Jürgen Schmidt、Carsten Milkowski、Dieter Strack

  DOI：10.1016/j.phytochem.2008.03.021

  日期：2008.6

  intermediate in the proposed random sequential bi-bi mechanism of catalysis. SMT-catalyzed formation of disinapoylglucose has been corroborated by docking studies with an established homology structure model that illustrates the possible binding of two 1-O-sinapoyl-beta-glucose molecules in the active site and the intermolecular reaction of the two glucose esters. The SMT gene is embedded in a tandem cluster

  对来自拟南芥的丝氨酸羧肽酶样 (SCPL) 1-O-sinapoyl-beta-glucose:l-malate sinapoyltransferase (SMT) 的催化特性的分析表明，该酶除了主要的 l-苹果酸sinapoylation 外，还具有少量水解和歧化活性，分别产生游离芥子酸和 1,2-二-O-芥子酰-β-葡萄糖。该酶从供体分子 1-O-sinapoyl-β-葡萄糖中释放芥子酸的能力表明在所提出的随机顺序双双催化机制中存在短寿命的酰基酶中间体。SMT 催化的 disinapoylglucose 形成已通过对接研究得到证实，已建立的同源结构模型说明了活性位点中两个 1-O-sinapoyl-β-葡萄糖分子的可能结合以及两种葡萄糖酯的分子间反应。SMT 基因嵌入五个 SCPL 芥子酰转移酶基因的串联簇中，这些基因编码具有高氨基酸序列同一性和部分重叠底物特异性的酶。我们假设在编码 SCPL