phytyl diphosphate

• 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: phytyl diphosphate
• 英文别名: phytyl pyrophosphate；phytyl-PP；Phytyl diphosphate(3-)；[oxido-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enoxy]phosphoryl] phosphate
• 化学式: C₂₀H₃₉O₇P₂
• 分子量: 453.473
• InChiKey: ITPLBNCCPZSWEU-PYDDKJGSSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  A 、 phytyl diphosphate 生成 geranylgeranyl diphosphate 、 AH₂
  参考文献：
  名称：

  Specific Partial Reduction of Geranylgeranyl Diphosphate by an Enzyme from the Thermoacidophilic Archaeon Sulfolobus acidocaldarius Yields a Reactive Prenyl Donor, Not a Dead-End Product

  摘要：

  摘要 香叶基纯碱还原酶来自 中的香叶基还原酶 可催化古生膜脂质前体中的香叶基还原基团还原，一般可还原所有四个双键。然而，当对二磷酸香叶酯进行还原酶反应时，四个双键中只有三个被还原。质谱分析和酸水解表明，在二磷酸香叶酯的部分还原产物中保留了烯丙基双键。因此，与完全还原的二磷酸植丹酰化合物不同，反应产物被证明是二磷酸植丹酰，它是古细菌前酰转移酶的底物。

  DOI：

  10.1128/jb.00082-08
• 作为产物：
  描述：

  植物醇 生成 phytyl diphosphate
  参考文献：
  名称：

  酶法合成甘氨醇

  摘要：

  大豆叶片中发现的新型戊烯醇甘露醇-9，-10和-11是通过十一碳烯基二磷酸合酶的作用通过植酸基和异戊烯基二磷酸合成，然后进行酸性磷酸酶处理而合成的。

  DOI：

  10.1016/0040-4039(91)80865-4

文献信息

• 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。
• Vitamin E biosynthesis: functional characterization of the monocot homogentisate geranylgeranyl transferase
  作者：Wenyu Yang、Rebecca E. Cahoon、Sarah C. Hunter、Chunyu Zhang、Jixiang Han、Trissa Borgschulte、Edgar B. Cahoon

  DOI：10.1111/j.1365-313x.2010.04417.x

  日期：2011.1

  The biosynthesis of the tocotrienol and tocopherol forms of vitamin E is initiated by prenylation of homogentisate. Geranylgeranyl diphosphate (GGDP) is the prenyl donor for tocotrienol synthesis, whereas phytyl diphosphate (PDP) is the prenyl donor for tocopherol synthesis. We have previously shown that tocotrienol synthesis is initiated in monocot seeds by homogentisate geranylgeranyl transferase (HGGT). This enzyme is related to homogentisate phytyltransferase (HPT), which catalyzes the prenylation step in tocopherol synthesis. Here we show that monocot HGGT is localized in the plastid and expressed primarily in seed endosperm. Despite the close structural relationship of monocot HGGT and HPT, these enzymes were found to have distinct substrate specificities. Barley (Hordeum vulgare cv. Morex) HGGT expressed in insect cells was six times more active with GGDP than with PDP, whereas the Arabidopsis HPT was nine times more active with PDP than with GGDP. However, only small differences were detected in the apparent K_m values of barley HGGT for GGDP and PDP. Consistent with its in vitro substrate properties, barley HGGT generated a mixture of tocotrienols and tocopherols when expressed in the vitamin E‐null vte2‐1 mutant lacking a functional HPT. Relative levels of tocotrienols and tocopherols produced in vte2‐1 differed between organs and growth stages, reflective of the composition of plastidic pools of GGDP and PDP. In addition, HGGT was able to functionally substitute for HPT to rescue vte2‐1‐associated phenotypes, including reduced seed viability and increased fatty acid oxidation of seed lipids. Overall, we show that monocot HGGT is biochemically distinct from HPT, but can replace HPT in important vitamin E‐related physiological processes.

  摘要维生素 E 的生育三烯酚和生育酚形式的生物合成是通过同戊烯二酸的前炔化作用开始的。香叶基二磷酸甘油酯（GGDP）是生育三烯酚合成的前酰供体，而生育酚合成的前酰供体是植烯醇二磷酸酯（PDP）。我们之前已经证明，在单子叶植物种子中，生育三烯酚的合成是由同源戊二酸龙葵酰转移酶（HGGT）启动的。这种酶与催化生育酚合成中的前酰化步骤的同源戊二酸植物酰基转移酶（HPT）有关。在这里，我们发现单子叶植物的 HGGT 定位于质体，主要在种子胚乳中表达。尽管单子叶植物 HGGT 和 HPT 的结构关系密切，但我们发现这些酶具有不同的底物特异性。在昆虫细胞中表达的大麦（Hordeum vulgare cv. Morex）HGGT 对 GGDP 的活性是对 PDP 的活性的六倍，而拟南芥 HPT 对 PDP 的活性是对 GGDP 的活性的九倍。然而，大麦 HGGT 对 GGDP 和 PDP 的表观 Km 值仅有微小差异。与其体外底物特性相一致的是，大麦 HGGT 在缺乏功能性 HPT 的维生素 E 缺失 vte2-1 突变体中表达时，会产生生育三烯酚和生育酚的混合物。在不同器官和生长阶段，vte2-1 产生的生育三烯酚和生育酚的相对水平不同，这反映了质体 GGDP 和 PDP 池的组成。此外，HGGT 能够在功能上替代 HPT 来挽救 vte2-1 相关的表型，包括种子活力降低和种子脂质的脂肪酸氧化增加。总之，我们的研究表明，单子叶植物 HGGT 在生物化学上不同于 HPT，但在重要的维生素 E 相关生理过程中可以替代 HPT。
• Reduced Activity of Geranylgeranyl Reductase Leads to Loss of Chlorophyll and Tocopherol and to Partially Geranylgeranylated Chlorophyll in Transgenic Tobacco Plants Expressing Antisense RNA for Geranylgeranyl Reductase1
  作者：Ryouichi Tanaka、Ulrike Oster、Elisabeth Kruse、Wolfhart Rüdiger、Bernhard Grimm

  DOI：10.1104/pp.120.3.695

  日期：1999.7.1

  The enzyme geranylgeranyl reductase (CHL P) catalyzes the reduction of geranylgeranyl diphosphate to phytyl diphosphate. We identified a tobacco (Nicotiana tabacum) cDNA sequence encoding a 52-kD precursor protein homologous to the Arabidopsis and bacterial CHL P. The effects of deficient CHL P activity on chlorophyll (Chl) and tocopherol contents were studied in transgenic plants expressing antisense CHL P RNA. Transformants with gradually reduced Chl P expression showed a delayed growth rate and a pale or variegated phenotype. Transformants grown in high (500 μmol m−2 s−1; HL) and low (70 μmol photon m−2 s−1; LL) light displayed a similar degree of reduced tocopherol content during leaf development, although growth of wild-type plants in HL conditions led to up to a 2-fold increase in tocopherol content. The total Chl content was more rapidly reduced during HL than LL conditions. Up to 58% of the Chl content was esterified with geranylgeraniol instead of phytol under LL conditions. Our results indicate that CHL P provides phytol for both tocopherol and Chl synthesis. The transformants are a valuable model with which to investigate the adaptation of plants with modified tocopherol levels against deleterious environmental conditions.

  酶类物质geranylgeranyl reductase (CHL P)催化将geranylgeranyl diphosphate还原为phytyl diphosphate。我们发现了一种烟草（Nicotiana tabacum）cDNA序列，编码了一个52 kD的前体蛋白，与拟南芥和细菌的CHL P同源。研究了表达反义CHL P RNA的转基因植物中，缺乏CHL P活性对叶绿素（Chl）和生育酚含量的影响。逐渐降低Chl P表达的转基因体表现出生长速度延迟和苍白或杂色表型。在高（500 μmol m−2 s−1; HL）和低（70 μmol photon m−2 s−1; LL）光照条件下生长的转基因体，在叶片发育期间显示出相似程度的生育酚含量降低，尽管野生型植物在HL条件下的生长导致生育酚含量增加了2倍。总的Chl含量在HL条件下比LL条件下更快速地降低。在LL条件下，高达58％的Chl含量与geranylgeraniol而不是phytol酯化。我们的结果表明，CHL P为生育酚和Chl合成提供phytol。这些转基因体是研究改变生育酚水平的植物对有害环境条件适应的有价值的模型。