玉米素核苷 | 6025-53-2

• 物质功能分类: 生物化工 - 核苷类药物 - 核苷中间体
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 玉米素核苷
• 中文别名: 玉精核糖甙；反式玉米素核苷；反式-9-(Β-D-呋喃核糖玉米素)；6-反式-4-羟基-3-甲基丁-2-烯基氨基嘌呤核苷；6-反式-4-羟基-3-甲基-丁-2-烯基氨基嘌呤核苷
• 英文名称: trans-zeatin 9-β-D-ribofuranoside
• 英文别名: zeatin-9-beta-D-ribofuranoside；N⁶-(4-Hydroxy-3-methyl-trans-2-butenyl)adenosine；9-β-D-ribofuranosylzeatin；trans-zeatin 9-riboside；trans-zeatine-riboside；trans-zeatin riboside；Zeatin riboside；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[[(E)-4-hydroxy-3-methylbut-2-enyl]amino]purin-9-yl]oxolane-3,4-diol
• CAS: 6025-53-2
• 化学式: C₁₅H₂₁N₅O₅
• 分子量: 351.362
• InChiKey: GOSWTRUMMSCNCW-HNNGNKQASA-N

物化性质

• 熔点：
  176-179 °C
• 沸点：
  485.17°C (rough estimate)
• 密度：
  1.2018 (rough estimate)
• 溶解度：
  乙酸：50 mg/mL，澄清，无色

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  29349990
• 危险品运输编号：
  OTH
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性方面，trans-Zeatinriboside 是细胞分裂素的一种前体，在木质素导管中主要以长距离信号的形式存在，调节叶片大小和分生组织的活性相关形状。

化学性质上，它为类白色至白色的结晶。

用途方面，它是作为中间体使用。

反应信息

• 作为反应物：
  描述：

  玉米素核苷 在 recombinant Solanum tuberosum cytokinin riboside phosphorylase 作用下， 以 aq. buffer 为溶剂， 反应 0.33h， 生成 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：

  利波腺苷 在 Salmonella typhimurium O₂-dependent tRNA modifying monooxgenase 、 双氧水 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 玉米素核苷
  参考文献：
  名称：

  Peroxide-Shunt Substrate-Specificity for the Salmonella typhimurium O₂-Dependent tRNA Modifying Monooxygenase (MiaE)

  摘要：

  Post-transcriptional modifications of tRNA are made to structurally diversify tRNA. These modifications alter noncovalent interactions within the ribosomal machinery, resulting in phenotypic changes related to cell metabolism, growth, and virulence. MiaE is a carboxylate bridged, nonheme diiron monooxygenase, which catalyzes the O-2-dependent hydroxylation of a hypermodified-tRNA nucleoside at position 37 (2-methylthio-N-6-isopentenyl-adenosine(37)-tRNA) [designated ms(2)i(6)A(37)]. In this work, recombinant MiaE was cloned from Salmonella typhimurium, purified to homogeneity, and characterized by UV-visible and dual-mode X-band EPR spectroscopy for comparison to other nonheme diiron enzymes. Additionally, three nucleoside substrate-surrogates (i(6)A, Cl(2)i(6)A, and ms(2)i(6)A) and their corresponding hydroxylated products (io(6)A, Cl(2)io(6)A, and ms(2)io(6)A) were synthesized to investigate the chemo- and stereospecificity of this enzyme. In the absence of the native electron transport chain, the peroxide-shunt was utilized to monitor the rate of substrate hydroxylation. Remarkably, regardless of the substrate (i(6)A, Cl(2)i(6)A, and ms(2)i(6)A) used in peroxide-shunt assays, hydroxylation of the terminal isopentenyl-C4-position was observed with >97% E-stereoselectivity. No other nonspecific hydroxylation products were observed in enzymatic assays. Steady-state kinetic experiments also demonstrate that the initial rate of MiaE hydroxylation is highly influenced by the substituent at the C2-position of the nucleoside base (v(0)/[E] for ms(2)i(6)A > i(6)A > Cl(2)i(6)A). Indeed, the >3-fold rate enhancement exhibited by MiaE for the hydroxylation of the free ms(2)i(6)A nucleoside relative to i(6)A is consistent with previous whole cell assays reporting the ms(2)io(6)A and io(6)A product distribution within native tRNA-substrates. This observation suggests that the nucleoside C2-substituent is a key point of interaction regulating MiaE substrate specificity:

  DOI：

  10.1021/bi4000832

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。
• Synthesis of [¹⁵ N₄ ] purine labeled cytokinin glycosides derived from zeatins and topolins with 9-β-<scp>d</scp> , 7-β-<scp>d</scp> -glucopyranosyl, or 9-β-<scp>d</scp> -ribofuranosyl group
  作者：Lenka Tranová、Jan Buček、Marek Zatloukal、Petr Cankař、Jakub Stýskala

  DOI：10.1002/jlcr.3702

  日期：2019.3

  Synthesis of [15 N4 ] purine labeled cytokinine glycosides derived from zeatins and topolins containing a 9-β-d, 7-β-d-glucopyranosyl, or 9-β-d-ribofuranosyl group is described. These N6 -substituted adenine derivatives are intended as internal analytic standards for phytohormone analysis. All labeled compounds were prepared from 6-chloro[15 N4 ]purine (1). The equilibrium reaction of 1 with acetobromo-α-d-glucose

  描述了 [15 N4 ] 嘌呤标记的细胞分裂素糖苷的合成，该糖苷源自玉米素和含有 9-β-d、7-β-d-吡喃葡萄糖基或 9-β-d-呋喃核糖基的玉米黄素。这些 N6 取代的腺嘌呤衍生物旨在作为植物激素分析的内部分析标准。所有标记化合物均由 6-氯[15 N4 ] 嘌呤 (1) 制备。1 与乙酰溴-α-d-葡萄糖的平衡反应得到异构体 7-β-d (3) 和 9-β-d (4) 氯代葡萄糖基前体，用相应的胺处理得到所需的标记细胞分裂素 7- β-d (6) 和 9-β-d (5) 吡喃葡萄糖苷。由 6-氯[15 N4 ] 嘌呤 (1) 制备的细胞分裂素 (7) 通过直接酶促转糖基化反应获得含有 9-β-d-呋喃核糖基团的细胞分裂素 (8)。
• 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，
• Structure-activity relationships of zeatin cytokinins produced by plant pathogenicPseudomonades
  作者：Antonio Evidente、Tozo Fujii、Nicola S. Iacobellis、Sergio Riva、Angelo Sisto、Giuseppe Surico

  DOI：10.1016/0031-9422(91)80055-6

  日期：——

  higher stimulating potency of chlorophyll synthesis when compared to zeatin and zeatin riboside, respectively. With regard to the synthetic analogues, any modification of the carbon skeleton of the side chain proved to influence the activity. In particular, the reduction of thetrans-double bond in 1′MeZ and its 9-β- d -riboside produces two diastereomeric dihydro derivatives, which show respectively a

  摘要 天然存在的新型细胞分裂素 1'-甲基玉米素 (1'MeZ) 及其 9-β-d-核糖苷 (1″MeZR) 和 2'-脱氧玉米素核苷 (2'deOZR)，以及它们通过化学或化学方法获得的衍生物。分析了酶促修饰在黄化黄瓜子叶中刺激叶绿素合成的能力。与显示出非常低的细胞分裂素活性的 2' deOZR 相比，与玉米素和玉米素核苷相比，1'MeZ 和 1"MeZR 分别显示出更高的叶绿素合成刺激效力。对于合成类似物，侧链碳骨架的任何修饰都证明会影响活性。特别是，1'MeZ 中反式双键的还原及其 9-β-d-核糖苷产生两种非对映异构二氢衍生物，这可能是由于新手性碳（侧链的 C-3）的立体化学而分别显示活性降低和完全丧失。1'MeZ 和 1”MeZR 的两种二氢衍生物的侧链 C-4 分别脱氧，产生两种非活性化合物。侧链羟基（C-4）的酰化以及核糖部分羟基的乙酰化对生物活性没有显着影响。
• Growth regulator and process for growth regulation of plant
  申请人：——

  公开号：US20040248737A1

  公开（公告）日：2004-12-09

  The present invention relates to growth regulators of a plant and processes for regulating the same, and more particularly, relates to a technique to regulate the growth of a plant using a substance which is friendly to the global environment. A growth regulator of a plant comprising NaHCO 3 and/or KHCO 3 as a principal active ingredient is provided.

  本发明涉及植物生长调节剂和调节植物生长调节剂的工艺，特别是涉及一种使用对全球环境友好的物质来调节植物生长的技术。植物生长调节剂由 NaHCO 3 和/或 KHCO 3 作为主要活性成分的植物生长调节剂。