赤霉素 A1 甲基酯 | 4747-53-9

• 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 A1 甲基酯
• 中文别名: 赤霉素A1甲基酯；赤霉素A1甲酯
• 英文名称: Gibberellin A1 methyl ester
• 英文别名: methyl (1R,2R,5S,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylate
• CAS: 4747-53-9；25274-39-9；87726-57-6
• 化学式: C₂₀H₂₆O₆
• 分子量: 362.423
• InChiKey: OHIXAJDQAXXFTE-QDEMZEMRSA-N

物化性质

• 熔点：
  233-236 °C (decomp)(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  557.4±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  赤霉素 A1 甲基酯 在 甲醇 、 铂 作用下， 生成 16ξ,17-Dihydro-GA₁-methylester
  参考文献：
  名称：

  Kawarada et al., Journal of the Agricultural Chemical Society of Japan, 1955, vol. 19, p. 278,279

  摘要：

  DOI：
• 作为产物：
  描述：

  赤霉素A3甲酯 在 sodium tetrahydroborate 、 重铬酸吡啶 、 copper(l) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 赤霉素 A1 甲基酯
  参考文献：
  名称：

  赤霉素A的制备9和A 20从赤霉酸

  摘要：

  使用三苯膦和四氯化碳，赤霉酸甲酯已通过3-epigibberellin A 1的甲酯转化为3β-氯代和3β，13-二氯代衍生物。用氢化三丁基锡氢化氯化物，得到赤霉素A 20和A 9为它们的甲酯。赤霉素A 9甲酯也由赤霉素A 4 / A 7混合物制备。定义了环A-不饱和酮的共轭还原的立体化学。

  DOI：

  10.1039/p19810000161

文献信息

• Plant hormones—I
  作者：J. MacMillan、J.C. Seaton、P.J. Suter

  DOI：10.1016/0040-4020(60)89008-4

  日期：1960.1

  The isolation of the growth-promoting acids, gibberellin A1 and gibberellin A5, from immature seed of Phaseolus multiflorus is described. The structure of gibberellin A5 is established as V by degradation and by its preparation from gibberellin A1.

  描述了从多花菜豆的未成熟种子中分离促进生长的酸，赤霉素A 1和赤霉素A 5。赤霉素A的结构5被确定为通过降解V和通过从赤霉素甲及其制备1。
• A Refined Method for the Removal of the Methoxymethyl (MOM) Protecting Group for Carbinols with Acidic Ion-Exchange Resin
  作者：Hideharu Seto、Lewis N. Mander

  DOI：10.1080/00397919208021548

  日期：1992.11

  Abstract The methoxymethyl protecting group for carbinols is best removed from acid-sensitive substrates by hydrolysis in aqueous methanol using a cationic exchange resin (Dowex-50W).

  摘要 甲醇的甲氧基甲基保护基团最好通过使用阳离子交换树脂 (Dowex-50W) 在甲醇水溶液中水解从酸敏感底物中去除。
• Methylenation of carbonyl compounds with ZnCH2Br2TiCl4. Application to gibberellins
  作者：Luciano Lombardo

  DOI：10.1016/s0040-4039(00)88728-6

  日期：1982.1

  A highly active species prepared from ZnCH2Br2TiCl4 reacted instantaneously with aldehydes and ketones to give methylenated products with exceptional selectivity.

  从ZnCH制备的高度活性种2溴2 TiCl 4与醛类和酮类，得到methylenated产品具有卓越的选择性瞬间反应。
• Preparation of gibberellins A9 and A20 from gibberellic acid
  作者：Zvitendo J. Duri、Braulio M. Fraga、James R. Hanson

  DOI：10.1039/p19810000161

  日期：——

  using triphenylphosphine and carbon tetrachloride. Hydrogenolysis of the chlorides with tributyltin hydride afforded gibberellins A20 and A9 as their methyl esters. Gibberellin A9 methyl ester was also prepared from the gibberellin A4/A7 mixture. The stereochemistry of the conjugate reduction of the ring-A-unsaturated ketone is defined.

  使用三苯膦和四氯化碳，赤霉酸甲酯已通过3-epigibberellin A 1的甲酯转化为3β-氯代和3β，13-二氯代衍生物。用氢化三丁基锡氢化氯化物，得到赤霉素A 20和A 9为它们的甲酯。赤霉素A 9甲酯也由赤霉素A 4 / A 7混合物制备。定义了环A-不饱和酮的共轭还原的立体化学。
• Methylation of Gibberellins by <i>Arabidopsis</i> GAMT1 and GAMT2
  作者：Marina Varbanova、Shinjiro Yamaguchi、Yue Yang、Katherine McKelvey、Atsushi Hanada、Roy Borochov、Fei Yu、Yusuke Jikumaru、Jeannine Ross、Diego Cortes、Choong Je Ma、Joseph P. Noel、Lew Mander、Vladimir Shulaev、Yuji Kamiya、Steve Rodermel、David Weiss、Eran Pichersky

  DOI：10.1105/tpc.106.044602

  日期：2007.2.27

  Arabidopsis thaliana GAMT1 and GAMT2 encode enzymes that catalyze formation of the methyl esters of gibberellins (GAs). Ectopic expression of GAMT1 or GAMT2 in Arabidopsis, tobacco (Nicotiana tabacum), and petunia (Petunia hybrida) resulted in plants with GA deficiency and typical GA deficiency phenotypes, such as dwarfism and reduced fertility. GAMT1 and GAMT2 are both expressed mainly in whole siliques (including seeds), with peak transcript levels from the middle until the end of silique development. Within whole siliques, GAMT2 was previously shown to be expressed mostly in developing seeds, and we show here that GAMT1 expression is also localized mostly to seed, suggesting a role in seed development. Siliques of null single GAMT1 and GAMT2 mutants accumulated high levels of various GAs, with particularly high levels of GA1 in the double mutant. Methylated GAs were not detected in wild-type siliques, suggesting that methylation of GAs by GAMT1 and GAMT2 serves to deactivate GAs and initiate their degradation as the seeds mature. Seeds of homozygous GAMT1 and GAMT2 null mutants showed reduced inhibition of germination, compared with the wild type, when placed on plates containing the GA biosynthesis inhibitor ancymidol, with the double mutant showing the least inhibition. These results suggest that the mature mutant seeds contained higher levels of active GAs than wild-type seeds.

  拟南芥GAMT1和GAMT2编码催化赤霉素（GAs）的甲酯形成的酶。在拟南芥、烟草（Nicotiana tabacum）和矮牵牛（Petunia hybrida）中外源表达GAMT1或GAMT2导致植物缺乏GA和典型的GA缺乏表型，如侏儒和生育力降低。GAMT1和GAMT2主要在整个角果（包括种子）中表达，峰值转录水平从角果发育的中期到末期。在整个角果中，GAMT2先前被证明主要在发育的种子中表达，我们在这里显示GAMT1表达也主要定位于种子，暗示其在种子发育中的作用。单个GAMT1和GAMT2突变体的角果积累了各种GAs的高水平，双突变体中GA1的水平尤为高。野生型角果中未检测到甲基化GAs，表明GAMT1和GAMT2对GAs的甲基化作用是使GAs失活并在种子成熟时启动其降解。当放置在含有GA生物合成抑制剂ancymidol的培养皿上时，纯合GAMT1和GAMT2缺失突变体的种子与野生型相比表现出较少的萌发抑制，双突变体的抑制最少。这些结果表明，成熟的突变体种子中含有比野生型种子更高水平的活性GAs。