phytylplastoquinol | 96480-20-5

• 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
• 英文名称: phytylplastoquinol
• 英文别名: Phytylplastoquinol；2,3-dimethyl-5-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]benzene-1,4-diol
• CAS: 96480-20-5
• 化学式: C₂₈H₄₈O₂
• 分子量: 416.688
• InChiKey: SUFZKUBNOVDJRR-WGEODTKDSA-N

物化性质

• 沸点：
  534.1±45.0 °C(Predicted)
• 密度：
  0.939±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phytylplastoquinol 在 chloroplast suspension SAM 作用下， 以 乙醇 、 硫酸 为溶剂， 反应 0.5h， 生成 天然维生素E
  参考文献：
  名称：

  2-Methyl-6-phytylquinol and 2,3-dimethyl-5-phytylquinol as precursors of tocopherol synthesis in spinach chloroplasts

  摘要：

  The incorporation of [Me(methyl)-14C] from SAM(S-adenosylmethionine)-[Me-14C] into precursors indicates the following sequence of tocopherol synthesis in spinach: 2-methyl-6-phytylquinol (6-phytyltoluquinol) (1a) .fwdarw. 2,3-dimethyl-5-phytylquinol (phytylplastoquinol) (2a) .fwdarw. .gamma.-tocopherol (5a) .fwdarw. .alpha.-tocopherol (6). 1a is particularly preferred to 2-methyl-5-phytylquinol (1b) and 2-methyl-3-phytylquinol (1c). 1a only forms 2a. 2a is converted to 6 via 5a and, to a lesser extent, 2,5-dimethyl-6-phylquinol (2b) to 6 via .beta.-tocopherol (5b). Trimethylphytylquinol (3) is not an intermediate in the formation of 6. All reactions are independent of light.

  DOI：

  10.1016/s0031-9422(00)81963-9
• 作为产物：
  描述：

  D-gamma-生育酚 生成 phytylplastoquinol
  参考文献：
  名称：

  Isolation of an Arabidopsis mutant lacking vitamin E and identification of a cyclase essential for all tocopherol biosynthesis

  摘要：

  生育酚（维生素E）是一种植物叶绿体脂质，被认为参与响应氧化应激。通过使用基于薄层色谱的筛选方法，从拟南芥（Arabidopsis thaliana）中分离出一个缺乏生育酚的突变体（vte1）。突变体植物缺乏所有四种生育酚形式，并且缺乏生育酚环化酶活性。通过遗传图谱分析vte1和基因组学方法，鉴定了ORF At4g32770作为生育酚环化酶的候选基因。在vte1中，At4g32770含有一个剪切位点突变，并且相应的mRNA表达减少。在大肠杆菌中表达VTE1导致产生具有高生育酚环化酶和生育三烯酚环化酶活性的蛋白质。VTE1序列与已知功能基因没有相似性，但与最近基于蔗糖转运缺陷1玉米突变体（sxd1）的可用性而分离出的SXD1基因相似。在最适生长条件下，vte1突变体的生长、叶绿素含量和光合量子产率与野生型相似。因此，生育酚的缺失对光合作用或植物生存力没有大的影响，表明其他抗氧化剂可以弥补生育酚的损失。在光氧化应激期间，与野生型相比，vte1的叶绿素含量和光合量子产率略有降低，表明生育酚在维持高光压力下的最佳光合速率方面可能发挥了潜在作用。

  DOI：

  10.1073/pnas.182330899

文献信息

• The Reaction Mechanism of Chromanol-Ring Formation Catalyzed by tocopherol cyclase from<i>Anabaena variabilis</i>K<scp>ÜTZING</scp>(<i>Cyanobacteria</i>)
  作者：Achim Stocker、Giusep Derungs、Wolf-Dietrich Woggon、Thomas Netscher、August Rüttimann、Robert K. Müller、Heinz Schneider、Louis J. Todaro

  DOI：10.1002/hlca.19940770705

  日期：1994.11.2

  Incubation of the synthetic 18O-labelled phytyl-hydroquinone (O4-18O)-2 with the tocopherol cyclase from Anabaena variabilis KÜTZING (Cyanobacteria) in D2O furnished the doubly labelled γ-tocopherol, (2R,3S,4′R,8′R)-(1-18O,3-2H)-1. The chirality at C(3) was determined by two independent routes providing interlocking evidence that the enzyme-catalyzed ring closure proceeds by si-protonation of the double

  合成的孵育18 O形标记的植基-氢醌（ø 4 - 18 O） - 2从生育酚环化酶多变鱼腥藻KÜTZING（蓝藻）在d 2 ö提供的双标记的γ生育酚，（2 - [R，3小号， 4' - [R，8' - [R） - （1- 18 O，3- 2 H） - 1。C（3）的手性由两个独立的途径确定，提供了互锁的证据，表明酶催化的闭环通过2的双键的si质子化而进行并伴随着对酚O原子的重新攻击。
• Nucleic acid sequences to proteins involved in tocopherol synthesis
  申请人：——

  公开号：US20030170833A1

  公开（公告）日：2003-09-11

  Nucleic acid sequences and methods are provided for producing plants and seeds having altered tocopherol content and compositions. The methods find particular use in increasing the tocopherol levels in plants, and in providing desirable tocopherol compositions in a host plant cell.

  提供核酸序列和方法，用于生产具有改变生育酚含量和组成的植物和种子。该方法特别适用于增加植物中的生育酚水平，并在宿主植物细胞中提供理想的生育酚组成。
• Nucleic acid sequences to proteins involved in isoprenoid synthesis
  申请人：Calgene LLC

  公开号：US06541259B1

  公开（公告）日：2003-04-01

  Nucleic acid sequences and methods are provided for producing plants and seeds having altered tocopherol content and compositions. The methods find particular use in increasing the tocopherol levels in plants, and in providing desirable tocopherol compositions in a host plant cell.

  提供了核酸序列和方法，用于生产具有改变生育酚含量和组成的植物和种子。该方法特别适用于增加植物中的生育酚水平，并在宿主植物细胞中提供理想的生育酚组成。
• NUCLEIC ACID SEQUENCES TO PROTEINS INVOLVED IN TOCOPHEROL SYNTHESIS
  申请人：Subramaniam Sai S.

  公开号：US20100216204A1

  公开（公告）日：2010-08-26

  Nucleic acid sequences and methods are provided for producing plants and seeds having altered tocopherol content and compositions. The methods find particular use in increasing the tocopherol levels in plants, and in providing desirable tocopherol compositions in a host plant cell.

  提供了核酸序列和方法，用于产生具有改变的生育酚含量和组成的植物和种子。该方法特别适用于增加植物中的生育酚水平，并在宿主植物细胞中提供理想的生育酚组成。
• Characterization of Tocopherol Cyclases from Higher Plants and Cyanobacteria. Evolutionary Implications for Tocopherol Synthesis and Function
  作者：Scott E. Sattler、Edgar B. Cahoon、Sean J. Coughlan、Dean DellaPenna

  DOI：10.1104/pp.103.024257

  日期：2003.8.1

  Tocopherols are lipophilic antioxidants synthesized exclusively by photosynthetic organisms and collectively constitute vitamin E, an essential nutrient for both humans and animals. Tocopherol cyclase (TC) catalyzes the conversion of various phytyl quinol pathway intermediates to their corresponding tocopherols through the formation of the chromanol ring. Herein, the molecular and biochemical characterization of TCs from Arabidopsis (VTE1 [VITAMIN E 1]), Zea mays (SXD1 [Sucrose Export Deficient 1]) and Synechocystis sp. PCC6803 (slr1737) are described. Mutations in the VTE1, SXD1, or slr1737 genes resulted in both tocopherol deficiency and the accumulation of 2,3-dimethyl-6-phytyl-1,4-benzoquinone (DMPBQ), a TC substrate. Recombinant SXD1 and VTE1 proteins are able to convert DMPBQ to γ-tocopherol in vitro. In addition, expression of maize SXD1 in a Synechocystis sp. PCC6803 slr1737 knockout mutant restored tocopherol synthesis, indicating that TC activity is evolutionarily conserved between plants and cyanobacteria. Sequence analysis identified a highly conserved 30-amino acid C-terminal domain in plant TCs that is absent from cyanobacterial orthologs. vte1-2 causes a truncation within this C-terminal domain, and the resulting mutant phenotype suggests that this domain is necessary for TC activity in plants. The defective export of Suc in sxd1 suggests that in addition to presumed antioxidant activities, tocopherols or tocopherol breakdown products also function as signal transduction molecules, or, alternatively, the DMPBQ that accumulates in sxd1 disrupts signaling required for efficient Suc export in maize.

  生物合成的脂溶性抗氧化剂生育酚仅由光合生物合成，共同构成维生素E，是人类和动物的必需营养素。生育酚环化酶（TC）通过形成色酚环催化各种植物醌途径中间体的转化为相应的生育酚。本文描述了来自拟南芥（VTE1 [维生素E 1]）、玉米（SXD1 [蔗糖导出缺陷1]）和Synechocystis sp. PCC6803（slr1737）的TC的分子和生化特性。VTE1、SXD1或slr1737基因的突变导致生育酚缺乏和2,3-二甲基-6-植酰基-1,4-苯醌（DMPBQ）的积累，这是TC底物。重组的SXD1和VTE1蛋白能够在体外将DMPBQ转化为γ-生育酚。此外，将玉米SXD1在Synechocystis sp. PCC6803 slr1737敲除突变体中表达可恢复生育酚合成，表明植物和蓝细菌之间的TC活性在进化上是保守的。序列分析确定了植物TC中高度保守的30个氨基酸C端结构域，而蓝细菌同源物中则不存在。vte1-2导致该C端结构域的截短，导致的突变表型表明该结构域对于植物中的TC活性是必需的。sxd1中的蔗糖缺陷表明，除了预期的抗氧化活性外，生育酚或生育酚降解产物还起到信号转导分子的作用，或者是sxd1中积累的DMPBQ干扰了玉米高效蔗糖导出所需的信号传递。