赤霉素 A13 | 2922-24-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 赤霉素 A13
• 中文别名: 赤霉素A13
• 英文名称: gibberellin GA₁₃
• 英文别名: GA₁₃；Gibberellin A(13)；Gibberellin A13；(1R,2S,3S,4S,5S,8R,9R,12R)-5-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadecane-2,4,8-tricarboxylic acid
• CAS: 2922-24-9
• 化学式: C₂₀H₂₆O₇
• 分子量: 378.422
• InChiKey: UYRCHWLYXIQJKK-HMRRIYTKSA-N

物化性质

• 沸点：
  545.2±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  赤霉素 A13 反应 3.0h， 生成 gibberellin GA13 7,19,20-trimethyl ester
  参考文献：
  名称：

  The Estenfication of Gibberellins with Dimethylformamide Dimethyl Acetal (DMFDMA)

  摘要：

  关键步骤是通过将更容易获取的吉贝雷尔酸（GA3、GA4、GA7和GA13）转化为它们的甲基酯来准备稀有的吉贝雷尔酸。DMFDMA被用作酯化试剂，以避免因其有毒、易爆和危险性而产生的重氮乙烷。观察到DMFDMA除了酯化外，还可用作乙酰化和差向异构试剂。

  DOI：

  10.1515/znb-1997-1015
• 作为产物：
  描述：

  (1R,2S,3S,4S,5S,8R,9R,12R)-8-甲酰基-5-羟基-4-甲基-13-亚甲基四环[10.2.1.0(1,9).0(3,8)]十五烷-2,4-二甲酸 在 Fusarium fujikuroi Δcpr mutant 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 赤霉素 A13
  参考文献：
  名称：

  电子传递蛋白对藤黑镰刀菌赤霉素单加氧酶催化反应的影响

  摘要：

  来自 Fujikuroi 镰刀菌的多功能细胞色素 P450 单加氧酶 P450-1 和 P450-2 分别催化赤霉素 (GA) 生物合成途径中 GA14 和 GA4 的形成。然而，与含有 CPR 的菌株相比，这些酶的活性在缺乏 NADPH:细胞色素 P450 氧化还原酶 (CPR) 的突变体中在质量和数量上是不同的。3beta-羟基化是野生型菌株中主要的 P450-1 活性，相对于 C-6 和 C-7 处的氧化，突变体中强烈降低，而 C19-GAs 的合成是由于 C-20 的氧化裂解P450-2 几乎不存在，而 C-20 醇、醛和羧酸衍生物积累。单加氧酶与替代电子传递蛋白的相互作用可以解释这些不同的产物分布。在没有心肺复苏术的情况下，P450-1 活性是 NADH 依赖性的，并受到细胞色素 b5 或添加的 FAD 的刺激。这些特性以及突变体中 P450-1 和 P450-2 的效率降低与细胞色素

  DOI：

  10.1016/j.phytochem.2007.08.026

文献信息

• GC-MS identification of endogenous gibberellins and gibberellin conjugates as their permethylated derivatives
  作者：Laurent Rivier、Paul Gaskin、Kum-yul S. Albone、Jake MacMillan

  DOI：10.1016/0031-9422(81)85157-6

  日期：1981.1

  preparing permethyl derivatives of GAs and GA-glucosides is described using NaH and MeI in DMF. The permethyl derivatives of the glucosides give sharp GC peaks and their MS provide information for the identification of the GA and carbohydrate moieties. The detection and characterization of endogenous GAs and GA-glycosides in pods of Phaseolus coccineus by GC-MS of permethylated extracts are described

  摘要 描述了在 DMF 中使用 NaH 和 MeI 制备 GAs 和 GA-葡萄糖苷的全甲基衍生物的简便方法。葡萄糖苷的全甲基衍生物产生尖锐的 GC 峰，它们的 MS 为鉴定 GA 和碳水化合物部分提供了信息。描述了通过全甲基化提取物的 GC-MS 检测和表征菜豆豆荚中的内源性 GA 和 GA-糖苷。描述了通过相同方法对碳水化合物、IAA、ABA 和细胞分裂素进行全甲基化。
• Some 19-norgibberell-16-enes as inhibitors of gibberellin plant hormone biosynthesis
  作者：Mark K. Baynham、James R. Hanson

  DOI：10.1016/s0040-4039(00)81811-0

  日期：1983.1

  Methyl ent-7-hydroxy-4β(H)-19(norgibberell-16-en-20-oate, the corresponding 7,20-diol and 20-desoxy derivative, have been prepared from gibberellins A13 and A14 respectively and shown to act as inhibitors of gibberellic acid biosynthesis in Gibberella fujikuroi; further investigation of the 7-hydroxy-20-methyl ester suggests that this may be acting at the ring contraction step.

  分别由赤霉素A 13和A 14制备了7-羟基-4β（H）-19（norgibberell-16-en-20-oate）甲酯，相应的7,20-二醇和20-脱氧衍生物可以用作富士赤霉菌中赤霉素生物合成的抑制剂；对7-羟基-20-甲基酯的进一步研究表明，这可能是在环收缩步骤中起作用的。
• Gibberellin A13 7-aldehyde: A proposed intermediate in the fungal biosynthesis of gibberellin A3
  作者：John R. Bearder、Jake MacMillan、Bernard O. Phinney、James R. Hanson、Douglas E.A. Rivett、Christine L. Willis

  DOI：10.1016/0031-9422(82)85182-0

  日期：1982.1

  Abstract Gibberellin A 13 7-aldehyde, previously proposed as an intermediate in the fungal biosynthesis of gibberellin A 3 , has been prepared from gibbere

  摘要 Gibberellin A 13 7-醛，以前提出作为真菌生物合成赤霉素 A 3 的中间体，已从赤霉素制备。
• Plant growth regulators
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0112629A1

  公开（公告）日：1984-07-04

  The salt of GA4 and/or GA7 with an amine of formula R1CH2NHR2 wherein R' is optionally substituted phenyl, thienyl or pyridyl and R2 is alkyl or alkynyl. The salts are useful in the preparation of GA4/GA7 and their separation from GA3.

  GA4 和/或 GA7 与式 R1CH2NHR2 的胺盐，其中 R' 是任选取代的苯基、噻吩基或吡啶基，R2 是烷基或炔基。这些盐有助于制备 GA4/GA7，并将它们从 GA3 中分离出来。
• Gibberellins in seedlings and flowering trees of Prunus avium L.
  作者：Patrick S. Blake、Gordon Browning、Lynda J. Benjamin、Lewis N. Mander

  DOI：10.1016/s0031-9422(99)00597-x

  日期：2000.2

  Extracts of acids from mature seeds, germinating seeds, first, second and third year seedlings as well as mature, flowering trees of sweet cherry (Prunus avium L. cv. Stella) were analysed by gas chromatography-mass spectrometry. The presence of the known gibberellins (GAs) GA(1) (1), GA(3) (4), GA(5) (7), GA(8) (11), GA(19) (14), GA(20) (12), GA(29) (13), GA(32) (5), GA(85) (2), GA(86) (3) and GA(87) (6) was confirmed by comparison of their mass spectra and Kovats retention indices with those of standards or literature values. In addition, 16 alpha,17-dihydrodihydroxy GA(25) (16) was identified and its stereochemistry confirmed by rational synthesis. The 12 alpha,13-dihydroxy GAs, GA(32) (5), GA(85) (2), GA(86) (3) and GA(87) (6), were detected in mature seeds, germinating seeds and young seedlings, but not in flowering plants. The 13-hydroxy GAs, GA(1) (1) and GA(3) (4), were present in germinating seeds and, in addition to these, GA(5) (7), GA(8) (11), GA(19) (14), GA(20) (12) and GA(29) (13) were detected in seedlings and mature flowering plants. In germinating seeds and seedlings (while the plants were growing actively), concentrations of the 12 alpha,13-dihydroxy GAs, measured by bioassay, declined and those of the 13-hydroxy GAs increased. The results are discussed with reference to the known and predicted effects of the GAs on the vegetative growth and flowering of P. avium plants. (C) 2000 Elsevier Science Ltd. All rights reserved.