Dihydrozeatin-9-beta-D-ribofuranoside | 22663-55-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: Dihydrozeatin-9-beta-D-ribofuranoside
• 英文别名: dihydrozeatin riboside；N⁶-(4-hydroxy-3-methyl-butyl)-adenosine；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[(4-hydroxy-3-methylbutyl)amino]purin-9-yl]oxolane-3,4-diol
• CAS: 22663-55-4
• 化学式: C₁₅H₂₃N₅O₅
• mdl: MFCD00056979
• 分子量: 353.378
• InChiKey: DBVVQDGIJAUEAZ-YXYADJKSSA-N

物化性质

• 熔点：
  167-169℃
• 沸点：
  708.8±70.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（轻微）、甲醇（非常轻微、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  Dihydrozeatin-9-beta-D-ribofuranoside 在 recombinant Solanum tuberosum cytokinin riboside phosphorylase 作用下， 以 aq. buffer 为溶剂， 反应 0.33h， 生成 DL-二氢玉米素
  参考文献：
  名称：

  A purine nucleoside phosphorylase in Solanum tuberosum L. (potato) with specificity for cytokinins contributes to the duration of tuber endodormancy

  摘要：

  StCKP1 （Solanum tuberosum 细胞分裂素核糖苷磷酸化酶）催化植物激素 CK（细胞分裂素）的 N9-核糖苷形式（嘌呤的一个子集）与其最具活性的游离碱基形式之间的相互转化。StCKP1 更喜欢 CK 而不是未取代的氨基嘌呤。该蛋白是在马铃薯块茎化匍匐茎尖的提取物中发现的，并通过亲和层析法从中分离出具有 CK 结合活性的蛋白。其 N 端氨基酸序列与一组 ESTs 的翻译产物相匹配，从而能够通过 RACE-PCR 获得完整的 mRNA 序列。预测的多肽包括一个可裂解的信号肽和嘌呤核苷磷酸化酶活性基团。对表达的蛋白质进行了嘌呤核苷磷酸化酶活性检测，检测对象为 CKs 和腺嘌呤/腺苷。在 1-磷酸核糖存在的情况下，异戊烯基腺嘌呤、反式玉米素、双氢玉米素和腺嘌呤被转化为核苷。与此相反，异戊烯基腺苷、反式玉米素核苷、二氢玉米素核苷和腺苷在 Pi 的存在下转化为其游离碱基。StCKP1 没有检测到核糖水解酶活性。有证据表明，StCKP1 在块茎中作为 CKs 的负调控因子具有活性，可通过冷可逆机制延长内眠期。

  DOI：

  10.1042/bj20130792
• 作为产物：
  描述：

  DL-二氢玉米素 、 D-ribose 5-phosphate 在 recombinant Solanum tuberosum cytokinin riboside phosphorylase 作用下， 以 aq. buffer 为溶剂， 反应 0.33h， 生成 Dihydrozeatin-9-beta-D-ribofuranoside
  参考文献：
  名称：

  A purine nucleoside phosphorylase in Solanum tuberosum L. (potato) with specificity for cytokinins contributes to the duration of tuber endodormancy

  摘要：

  StCKP1 （Solanum tuberosum 细胞分裂素核糖苷磷酸化酶）催化植物激素 CK（细胞分裂素）的 N9-核糖苷形式（嘌呤的一个子集）与其最具活性的游离碱基形式之间的相互转化。StCKP1 更喜欢 CK 而不是未取代的氨基嘌呤。该蛋白是在马铃薯块茎化匍匐茎尖的提取物中发现的，并通过亲和层析法从中分离出具有 CK 结合活性的蛋白。其 N 端氨基酸序列与一组 ESTs 的翻译产物相匹配，从而能够通过 RACE-PCR 获得完整的 mRNA 序列。预测的多肽包括一个可裂解的信号肽和嘌呤核苷磷酸化酶活性基团。对表达的蛋白质进行了嘌呤核苷磷酸化酶活性检测，检测对象为 CKs 和腺嘌呤/腺苷。在 1-磷酸核糖存在的情况下，异戊烯基腺嘌呤、反式玉米素、双氢玉米素和腺嘌呤被转化为核苷。与此相反，异戊烯基腺苷、反式玉米素核苷、二氢玉米素核苷和腺苷在 Pi 的存在下转化为其游离碱基。StCKP1 没有检测到核糖水解酶活性。有证据表明，StCKP1 在块茎中作为 CKs 的负调控因子具有活性，可通过冷可逆机制延长内眠期。

  DOI：

  10.1042/bj20130792

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，
• Plant growth regulators from ash strains ofPseudomonas syringae subsp.savastanoi
  作者：A. Evidente、E. Di Maio、A. Caponero、N. S. Iacobellis

  DOI：10.1007/bf01921754

  日期：1995.9

  Indole-3-acetic acid and its methyl ester have been isolated from cultures of Pseudomonas syringae subsp. savastanoi isolated from ash. However, typical strains produced only small amounts of the auxins, whereas relatively high amounts of the above phytohormones accumulated in the culture of an atypical strain. No cytokinins were isolated from cultures of the typical ash strains. Conversely, four cytokinins, namely dihydrozeatin and its 9-beta-riboside, trans-zeatin riboside and its 1 ''-methyl derivative, were found in an atypical strain culture.
• A purine nucleoside phosphorylase in <i>Solanum tuberosum</i> L. (potato) with specificity for cytokinins contributes to the duration of tuber endodormancy
  作者：Jennifer R. Bromley、Barbara J. Warnes、Christine A. Newell、Jamie C. P. Thomson、Celia M. James、Colin G. N. Turnbull、David E. Hanke

  DOI：10.1042/bj20130792

  日期：2014.3.1

  StCKP1 (Solanum tuberosum cytokinin riboside phosphorylase) catalyses the interconversion of the N9-riboside form of the plant hormone CK (cytokinin), a subset of purines, with its most active free base form. StCKP1 prefers CK to unsubstituted aminopurines. The protein was discovered as a CK-binding activity in extracts of tuberizing potato stolon tips, from which it was isolated by affinity chromatography. The N-terminal amino acid sequence matched the translation product of a set of ESTs, enabling a complete mRNA sequence to be obtained by RACE-PCR. The predicted polypeptide includes a cleavable signal peptide and motifs for purine nucleoside phosphorylase activity. The expressed protein was assayed for purine nucleoside phosphorylase activity against CKs and adenine/adenosine. Isopentenyladenine, trans-zeatin, dihydrozeatin and adenine were converted into ribosides in the presence of ribose 1-phosphate. In the opposite direction, isopentenyladenosine, trans-zeatin riboside, dihydrozeatin riboside and adenosine were converted into their free bases in the presence of Pi. StCKP1 had no detectable ribohydrolase activity. Evidence is presented that StCKP1 is active in tubers as a negative regulator of CKs, prolonging endodormancy by a chill-reversible mechanism.

  StCKP1 （Solanum tuberosum 细胞分裂素核糖苷磷酸化酶）催化植物激素 CK（细胞分裂素）的 N9-核糖苷形式（嘌呤的一个子集）与其最具活性的游离碱基形式之间的相互转化。StCKP1 更喜欢 CK 而不是未取代的氨基嘌呤。该蛋白是在马铃薯块茎化匍匐茎尖的提取物中发现的，并通过亲和层析法从中分离出具有 CK 结合活性的蛋白。其 N 端氨基酸序列与一组 ESTs 的翻译产物相匹配，从而能够通过 RACE-PCR 获得完整的 mRNA 序列。预测的多肽包括一个可裂解的信号肽和嘌呤核苷磷酸化酶活性基团。对表达的蛋白质进行了嘌呤核苷磷酸化酶活性检测，检测对象为 CKs 和腺嘌呤/腺苷。在 1-磷酸核糖存在的情况下，异戊烯基腺嘌呤、反式玉米素、双氢玉米素和腺嘌呤被转化为核苷。与此相反，异戊烯基腺苷、反式玉米素核苷、二氢玉米素核苷和腺苷在 Pi 的存在下转化为其游离碱基。StCKP1 没有检测到核糖水解酶活性。有证据表明，StCKP1 在块茎中作为 CKs 的负调控因子具有活性，可通过冷可逆机制延长内眠期。