trans-zeatin O-β-D-glucopyranoside | 56329-06-7

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: trans-zeatin O-β-D-glucopyranoside
• 英文别名: O-β-D-glucopyranosylzeatin；zeatin-O-glucoside；2-methyl-4-(7(9)H-purin-9-ylamino)-but-2-enyl β-D-glucopyranoside；O-beta-D-glucosyl-trans-zeatin；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-2-methyl-4-(7H-purin-6-ylamino)but-2-enoxy]oxane-3,4,5-triol
• CAS: 56329-06-7
• 化学式: C₁₆H₂₃N₅O₆
• 分子量: 381.389
• InChiKey: UUPDCCPAOMDMPT-HNVSNYHQSA-N

物化性质

• 沸点：
  638.7±65.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规定使用和储存，则不会分解，未有已知危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  trans-zeatin O-β-D-glucopyranoside 在 β-glucosidase 作用下， 反应 3.0h， 生成 N6-异戊烯基腺嘌呤
  参考文献：
  名称：

  Dolichos lablab 未成熟种子中的细胞分裂素

  摘要：

  摘要 五种细胞分裂素、反式-玉米素、9-β-d-呋喃核糖基-反式-玉米素、9-β-d-呋喃核糖基-顺式-玉米素、6-(反式-4-O-β-d-吡喃葡萄糖基-3-甲基-2-丁烯基氨基)嘌呤和6-(反式-4-O-β-d-吡喃葡萄糖基-3-甲基-2-丁烯基氨基)-9-β-d-呋喃核糖嘌呤从Dolichos lablab的未成熟种子中鉴定出来。

  DOI：

  10.1016/0031-9422(81)85156-4
• 作为产物：
  描述：

  玉米素 、 UDP-glucose 生成 氢(+1)阳离子 、 trans-zeatin O-β-D-glucopyranoside 、 UDP
  参考文献：
  名称：

  Zeatin Glycosylation Enzymes in Phaseolus

  摘要：

  使用硫酸铵沉淀法，结合亲和色谱和阴离子交换色谱，将一种催化菜豆未成熟胚中O-葡萄糖基玉米素形成的酶纯化了2500倍。该酶以反式玉米素为底物（K m为28微摩尔），但不以顺式玉米素、核糖基玉米素或二氢玉米素为底物。UDP-葡萄糖和UDP-木糖均可作为糖基供体，其K m分别为0.2和2.7毫摩尔，用于形成O-葡萄糖基玉米素和O-木糖基玉米素。相比之下，通过相同方法从普通菜豆胚中分离的UDP-木糖-玉米素：O-木糖基转移酶（JE Turner、DWS Mok、MC Mok、G Shaw [1987] Proc Natl Acad Sci USA 84: 3714-3717）仅以UDP-木糖为供体底物，且玉米素和UDP-木糖的K m都低得多（分别为2和3微摩尔）。两种酶在亲和色谱柱上的行为和分子量（约M r为44,000道尔顿）相似。底物竞争实验和阴离子交换高效液相色谱法分离酶的结果表明，在上述两种菜豆的胚中，存在一种独特的玉米素O-糖基化酶。

  DOI：

  10.1104/pp.90.4.1316

文献信息

• Derivatization for LC-Electrospray Ionization-MS:  A Tool for Improving Reversed-Phase Separation and ESI Responses of Bases, Ribosides, and Intact Nucleotides
  作者：Anders Nordström、Petr Tarkowski、Danuse Tarkowska、Karel Dolezal、Crister Åstot、Göran Sandberg、Thomas Moritz

  DOI：10.1021/ac0499017

  日期：2004.5.1

  We have developed a method for analyzing polar compounds by reversed-phase LC-ESI-MS following esterification of the analytes' free hydroxyl groups with propionyl or benzoyl acid anhydride. The method was applied to members of the plant hormone group cytokinins, which includes adenine bases, ribosides/glycosides, and nucleotides substituted at N-6 with an isoprenoid side chain, spanning a wide range of polarity. It was also used to analyze other compounds of biological importance, e.g., the nucleotides AMP, ADP, and ATP. The formation of more hydrophobic derivatives had a significant impact on two aspects of the analysis. The retention on a reversed-phase material was greatly increased without the use of any acetate/formate buffer or ion pairing reagent, and the ESI response was enhanced, due to the higher surface activities of the derivatives. Detection limits of propionylated cytokinins were in the high-attomole to low-femtomole range, an improvement by factors of 10−100 compared to previously reported figures. Using an automated SPE-based purification method, 12 endogenous cytokinins were quantified in extracts from 20- to 100-mg samples of leaves (from the plant Arabidopsis thaliana) with high accuracy and precision. Furthermore, the chromatographic properties of the benzoylated AMP, ADP, and ATP in the reversed-phase LC−MS system were much better in terms of retention, separation, and sensitivity than those of their underivatized counterparts, even without the use of any ion pairing reagent. Our data show that derivatization followed by LC-ESI-MS is an effective strategy for analyzing low molecular weight compounds, enabling compounds with a wide range of polarity to be determined in a single-injection LC−MS analysis.

  我们已经开发了一种分析极性化合物的方法，即在分析物的自由羟基上进行丙酸酐或苯甲酸酐的酯化反应后，进行反相液相-电喷雾-质谱（LC-ESI-MS）分析。该方法应用于植物激素类细胞分裂素的成员，包括腺嘌呤碱基、核糖核苷/糖苷以及在N-6位带有异戊二烯侧链的核苷酸，这些物质的极性范围广泛。该方法还被用于分析其他具有生物学重要性的化合物，例如核苷酸 AMP、ADP 和 ATP。形成更具疏水性的衍生物对分析的两个方面产生了重大影响。在不使用任何乙酸盐/甲酸盐缓冲液或离子配对试剂的情况下，保留在反相材料上的时间大大增加，并且由于衍生物的较高表面活性，ESI响应性增强。丙酸酰化的细胞分裂素的检测限在高位阿托摩尔到低位飞摩尔范围，相较于先前报道的数据，有了10至100倍的改进。使用自动化的SPE基净化方法，从植物拟南芥叶子的20至100毫克样品中提取的12种内源性细胞分裂素，能够以高度的准确性和精确性进行定量。此外，在反相LC-MS系统中，苯甲酸酰化的AMP、ADP和ATP的色谱特性在保留、分离和灵敏度方面远优于未经衍生的对应物，即便没有使用任何离子配对试剂。我们的数据显示，衍生化后进行LC-ESI-MS分析是分析低分子量化合物的一种有效策略，能够在单次注射LC-MS分析中测定极性范围广泛的化合物。
• Precolumn derivatization and capillary liquid chromatographic/frit-fast atom bombardment mass spectrometric analysis of cytokinins inArabidopsis thaliana
  作者：Crister Åstot、Karel Dolezal、Thomas Moritz、Göran Sandberg

  DOI：10.1002/(sici)1096-9888(199809)33:9<892::aid-jms701>3.0.co;2-n

  日期：1998.9

  New cytokinin derivatives with high surface activity were developed for capillary liquid chromatography/frit-fast atom bombardment (FAB) mass spectrometry. Propionyl ester derivatives of cytokinin nucleosides and glucosides and benzylamine derivatives of cytokinin bases gave stronger [M + H]+ ion currents than the underivatized compounds. In trace analysis by selective reaction monitoring, low (fmole)

  已开发出具有高表面活性的新型细胞分裂素衍生物，用于毛细管液相色谱/玻璃料原子轰击（FAB）质谱。细胞分裂素核苷和葡糖苷的丙酸酯衍生物和细胞分裂素碱的苄胺衍生物比未衍生化合物提供更强的[M + H] +离子流。在通过选择性反应监测进行的痕量分析中，发现了较低的（fmole）检测限。在通过B / E链接扫描进行的定性分析中，由于存在碎片离子，该衍生物还提供了更多的光谱信息，可诊断未衍生化合物光谱中不存在的核苷和葡糖苷的糖部分。拟议的FAB方法用于鉴定和定量拟南芥中的10种类异戊二烯细胞分裂素，包括游离碱，核苷，
• Zeatin Glycosylation Enzymes in <i>Phaseolus</i>
  作者：Susan C. Dixon、Ruth C. Martin、Machteld C. Mok、Gordon Shaw、David W. S. Mok

  DOI：10.1104/pp.90.4.1316

  日期：1989.8.1

  An enzyme catalyzing the formation of O-glucosylzeatin in immature embryos of Phaseolus lunatus was purified 2500-fold using ammonium sulfate precipitation followed by affinity and anion exchange chromatography. The enzyme uses trans-zeatin as substrate (K  m 28 micromolar) but not cis-zeatin, ribosylzeatin, or dihydrozeatin. Both UDP-glucose and UDP-xylose can serve as glycosyl donors, with K  ms of 0.2 and 2.7 millimolar, respectively, for the formation of O-glucosylzeatin and O-xylosylzeatin. In comparison, the UDPxylose-zeatin:O-xylosyltransferase (JE Turner, DWS Mok, MC Mok, G Shaw [1987] Proc Natl Acad Sci USA 84: 3714-3717) isolated by the same procedures from P. vulgaris embryos uses only UDP-xylose as donor substrate and the K  ms for both zeatin and UDP-xylose are much lower (2 and 3 micromolar, respectively). The chromatographic behavior on affinity columns and molecular weights (approximate M  r 44,000 daltons) of the two enzymes are similar. Results from substrate competition experiments and enzyme separation by anion exchange HPLC indicate a single, distinct, zeatin O-glycosylation enzyme occurs in embryos of each of these Phaseolus species.

  使用硫酸铵沉淀法，结合亲和色谱和阴离子交换色谱，将一种催化菜豆未成熟胚中O-葡萄糖基玉米素形成的酶纯化了2500倍。该酶以反式玉米素为底物（K m为28微摩尔），但不以顺式玉米素、核糖基玉米素或二氢玉米素为底物。UDP-葡萄糖和UDP-木糖均可作为糖基供体，其K m分别为0.2和2.7毫摩尔，用于形成O-葡萄糖基玉米素和O-木糖基玉米素。相比之下，通过相同方法从普通菜豆胚中分离的UDP-木糖-玉米素：O-木糖基转移酶（JE Turner、DWS Mok、MC Mok、G Shaw [1987] Proc Natl Acad Sci USA 84: 3714-3717）仅以UDP-木糖为供体底物，且玉米素和UDP-木糖的K m都低得多（分别为2和3微摩尔）。两种酶在亲和色谱柱上的行为和分子量（约M r为44,000道尔顿）相似。底物竞争实验和阴离子交换高效液相色谱法分离酶的结果表明，在上述两种菜豆的胚中，存在一种独特的玉米素O-糖基化酶。
• Cytokinins in immature seeds of Dolichos lablab
  作者：Takao Yokota、Junichi Ueda、Nobutaka Takahashi

  DOI：10.1016/0031-9422(81)85156-4

  日期：1981.1

  Abstract Five cytokinins, trans -zeatin, 9-β- d -ribofuranosyl- trans -zeatin, 9-β- d -ribofuranosyl- cis -zeatin, 6-( trans -4- O -β- d -glucopyranosyl-3-methyl-2-butenylamino)purine and 6-( trans -4- O -β- d -glucopyranosyl-3-methyl-2-butenylamino)-9-β- d -ribofuranosylpurine were identified from immature seeds of Dolichos lablab .

  摘要 五种细胞分裂素、反式-玉米素、9-β-d-呋喃核糖基-反式-玉米素、9-β-d-呋喃核糖基-顺式-玉米素、6-(反式-4-O-β-d-吡喃葡萄糖基-3-甲基-2-丁烯基氨基)嘌呤和6-(反式-4-O-β-d-吡喃葡萄糖基-3-甲基-2-丁烯基氨基)-9-β-d-呋喃核糖嘌呤从Dolichos lablab的未成熟种子中鉴定出来。
• N-Glucosylation of Cytokinins by Glycosyltransferases of Arabidopsis thaliana
  作者：Bingkai Hou、Eng-Kiat Lim、Gillian S. Higgins、Dianna J. Bowles

  DOI：10.1074/jbc.m409569200

  日期：2004.11

  Cytokinins are plant hormones that can be glucosylated to form O-glucosides and N-glucosides. The glycoconjugates are inactive and are thought to play a role in homeostasis of the hormones. Although O-glucosyltransferases have been identified that recognize cytokinins, the enzymes involved in N-glucosylation have not been identified even though the process has been recognized for many years. This study utilizes a screening strategy in which 105 recombinant glycosyltransferases (UGTs) of Arabidopsis have been analyzed for catalytic activity toward the classical cytokinins: trans-zeatin, dihydrozeatin, N-6-benzyladenine, N-6-isopentenyladenine, and kinetin. Five UGTs were identified in the screen. UGT76C1 and UGT76C2 recognized all cytokinins and glucosylated the hormones at the N-7 and N-9 positions. UGT85A1, UGT73C5, and UGT73C1 recognized trans-zeatin and dihydrozeatin, which have an available hydroxyl group for glucosylation and formed the O-glucosides. The biochemical characteristics of the N-glucosyltransferases were analyzed, and highly effective inhibitors of their activities were identified. Constitutive overexpression of UGT76C1 in transgenic Arabidopsis confirmed that the recombinant enzyme functioned in vivo to glucosylate cytokinin applied to the plant. The role of the N-glucosyltransferases in cytokinin metabolism is discussed.