2-((7R:11R)-trans-phytyl)-naphthoquinone-(1.4) | 34625-86-0

• 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: 2-((7R:11R)-trans-phytyl)-naphthoquinone-(1.4)
• 英文别名: 2-((7R:11R)-trans-Phytyl)-naphthochinon-(1.4)；2-Phytyl-1,4-naphthoquinone；2-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione
• CAS: 34625-86-0
• 化学式: C₃₀H₄₄O₂
• 分子量: 436.678
• InChiKey: UDYIPZFWVJJQJF-KQPZCCJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((7R:11R)-trans-phytyl)-naphthoquinone-(1.4) 、 氢(+1)阳离子 、 NADPH(4-) 生成 2-Phytyl-1,4-dihydroxynaphthalene 、 NADP⁺
  参考文献：
  名称：

  叶绿体脂滴 II 型 NAD(P)H 醌氧化还原酶对于异戊二烯醌代谢和维生素 K1 积累至关重要。

  摘要：

  脂滴是真核生物中普遍存在的细胞结构，是脂质代谢所必需的。目前对除油体以外的植物脂滴知之甚少。在这里，我们定义了叶绿体脂滴（质体球）在能量和异戊二烯醌代谢中的双重作用。异戊二烯醌--plastoquinone、plastochromanol-8、phylloquinone（维生素K(1)）和生育酚（维生素E）-部分存储在plastoglobules 中。这项工作表明 NAD(P)H 脱氢酶 C1 (NDC1) (At5g08740)，一种 II 型 NAD(P)H 醌氧化还原酶，与质体球结合。NDC1 在体外减少质体醌类似物，并通过减少质体球的质体醌储库影响体内总质体醌库的整体氧化还原状态。最后，

  DOI：

  10.1073/pnas.1104790108
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 四氯化碳 、 溴 作用下， 生成 2-((7R:11R)-trans-phytyl)-naphthoquinone-(1.4)
  参考文献：
  名称：

  合成2-苯基萘酚-1，4

  摘要：

  DOI：

  10.1002/hlca.19400230178

文献信息

• Inactivation and deficiency of core proteins of photosystems I and II caused by genetical phylloquinone and plastoquinone deficiency but retained lamellar structure in a T‐DNA mutant of Arabidopsis
  作者：Hiroshi Shimada、Ryoichi Ohno、Masaru Shibata、Isamu Ikegami、Kiyoshi Onai、Masa‐aki Ohto、Ken‐ichiro Takamiya

  DOI：10.1111/j.1365-313x.2004.02326.x

  日期：2005.2

  Phylloquinone, a substituted 1,4‐naphthoquinone with an 18‐carbon‐saturated phytyl tail, functions as a bound one‐electron carrier cofactor at the A₁ site of photosystem I (PSI). A Feldmann tag line mutant, no. 2755 (designated as abc4 hereafter), showed pale‐green young leaves and white old leaves. The mutated nuclear gene encoded 1,4‐dihydroxy‐2‐naphtoic acid phytyltransferase, an enzyme of phylloquinone biosynthesis, and high‐performance liquid chromatography analysis revealed that the abc4 mutant contained no phylloquinone, and only about 3% plastoquinone. Photooxidation of P700 of PSI in the abc4 mutant was not observed, and reduced‐versus‐oxidized difference spectroscopy indicated that the abc4 mutant had no P700. The maximum quantum yield of photosystem II (PSII) in the abc4 mutant was much decreased, and the electron transfer from PSII to PSI in the abc4 mutant did not occur. For the pale‐green leaves of the abc4 mutant plant, the ultrastructure of the chloroplasts was almost the same as that of the wild‐type plant. However, the chloroplasts in the albino leaves of the mutant were smaller and had a lot of grana thylakoids and few stroma thylakoids. The amounts of PSI and PSII core subunits in the abc4 mutant were significantly decreased compared with those in the wild type. These results suggested that a deficiency of phylloquinone in PSI caused the abolishment of PSI and a partial defect of PSII due to a significant decrease of plastoquinone, but did not influence the ultrastructure of the chloroplasts in young leaves.

  摘要 苝酮是一种具有 18 碳饱和苝基尾部的取代 1,4-萘醌，在光合系统 I（PSI）的 A1 位点上起结合单电子载体辅助因子的作用。一个编号为 2755 的费尔德曼标记线突变体（以下称为 abc4）显示出淡绿色的嫩叶和白色的老叶。突变的核基因编码 1,4-二羟基-2-萘乙酸酞基转移酶（一种植物醌生物合成酶），高效液相色谱分析显示，abc4 突变体不含植物醌，只含有约 3% 的质醌。在abc4突变体中没有观察到PSI的P700发生光氧化，还原与氧化差分光谱显示abc4突变体没有P700。在abc4突变体中，光系统II（PSII）的最大量子产率大大降低，并且在abc4突变体中没有发生从PSII到PSI的电子传递。在abc4突变体的淡绿色叶片中，叶绿体的超微结构与野生型植株几乎相同。然而，突变体白化叶片中的叶绿体较小，且颗粒状叶绿体较多，基质状叶绿体较少。与野生型相比，abc4 突变体中 PSI 和 PSII 核心亚基的数量明显减少。这些结果表明，由于质醌的大量减少，PSI中的质醌缺乏导致了PSI的废止和PSII的部分缺陷，但并不影响幼叶叶绿体的超微结构。
• A Dedicated Type II NADPH Dehydrogenase Performs the Penultimate Step in the Biosynthesis of Vitamin K1 in S<i>ynechocystis</i> and Arabidopsis
  作者：Abdelhak Fatihi、Scott Latimer、Stefan Schmollinger、Anna Block、Patrick H. Dussault、Wim F.J. Vermaas、Sabeeha S. Merchant、Gilles J. Basset

  DOI：10.1105/tpc.15.00103

  日期：2015.7.8

  demethylated precursor of vitamin K is strictly dependent on the reduced form of its naphthoquinone ring. NDC1 was shown to catalyze such a prerequisite reduction by using NADPH and demethylphylloquinone as substrates and flavine adenine dinucleotide as a cofactor. NDC1 displayed Michaelis-Menten kinetics and was markedly inhibited by dicumarol, a competitive inhibitor of naphthoquinone oxidoreductases. These

  拟南芥NAD（P）H脱氢酶C1（NDC1; At5g08740）的突变导致去甲基叶醌的积累，后者是维生素K1的晚期生物合成中间体。基因共表达和系统发育组学分析表明，在整个原核和真核世系中，维生素K生物合成与NDC1同源物之间存在保守的功能关联。编码一种这样的同源物的集胞藻ndbB的缺失导致与在蓝细菌脱甲基萘醌甲基转移酶敲除中观察到的那些缺陷相同的缺陷。纯化的脱甲基萘醌甲基转移酶的化学模型和分析表明，凭借S-腺苷-1-甲硫氨酸的强亲电性质，维生素K脱甲基前体的甲基化反应严格取决于其萘醌环的还原形式。NDC1被证明可以催化这种先决条件的降低，方法是使用NADPH和去甲基叶绿体醌作为底物，黄酮腺嘌呤二核苷酸作为辅因子。NDC1表现出Michaelis-Menten动力学，并被敌萘醌（一种竞争性的萘醌氧化还原酶抑制剂）显着抑制。这些数据表明，去甲基萘醌环的还原代表了维生素K生物合成途径中的一个真实
• Extensions of the Vitamin K₁ Synthesis
  作者：Louis F. Fieser、Max Tishler、Norman L. Wendler

  DOI：10.1021/ja01867a065

  日期：1940.10
• Recruitment of a Foreign Quinone into the A1 Site of Photosystem I
  作者：T.Wade Johnson、Gaozhong Shen、Boris Zybailov、Derrick Kolling、Ricardo Reategui、Steve Beauparlant、Ilya R. Vassiliev、Donald A. Bryant、A.Daniel Jones、John H. Golbeck、Parag R. Chitnis

  DOI：10.1074/jbc.275.12.8523

  日期：2000.3

  Genes encoding enzymes of the biosynthetic pathway leading to phylloquinone, the secondary electron acceptor of photosystem (PS) I, were identified in Synechocystis sp, PCC 6803 by comparison with genes encoding enzymes of the menaquinone biosynthetic pathway in Escherichia coli, Targeted inactivation of the menA and menB genes, which code for phytyl transferase and 1,4-dihydroxy-2-naphthoate synthase, respectively, prevented the synthesis of phylloquinone, thereby confirming the participation of these two gene products in the biosynthetic pathway. The menA and menB mutants grow photoautotrophically under low light conditions (20 mu E m(-2) s(-1)), with doubling times twice that of the mild type, but they are unable to grow under high light conditions (120 mu E m(-2) s(-1)). The menA and menB mutants grow photoheterotrophically on media supplemented with glucose under low light conditions, with doubling times similar to that of the wild type, but they are unable to grow under high light conditions unless atrazine is present to inhibit PS II activity. The level of active PS II per cell in the menA and menB mutant strains is identical to that of the wild type, but the level of active PS I is about 50-60% that of the wild type as assayed by low temperature fluorescence, P700 photoactivity, and electron transfer rates. PS I complexes isolated from the menA and menB mutant strains contain the full complement of polypeptides, show photoreduction of F-A and F-B at 15 K, and support 82-84% of the wild type rate of electron transfer from cytochrome c(6) to flavodoxin, HPLC analyses show high levels of plastoquinone-g in PS I complexes from the menA and menB mutants but not from the wild type. We propose that in the absence of phylloquinone, PS I recruits plastoquinone-g into the A(1) site, where it functions as an efficient cofactor in electron transfer from A(0) to the iron-sulfur clusters.
• CH213346
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