7,7',8,8',11,11',12,12'-八氢-psi,psi-胡罗卜素 | 13920-14-4

• 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: 7,7',8,8',11,11',12,12'-八氢-psi,psi-胡罗卜素
• 中文别名: 15-顺式-八氢番茄红素
• 英文名称: phytofluene
• 英文别名: Phytoen；phytoene；15-cis-Phytoene；(6E,10E,14E,16Z,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,14,16,18,22,26,30-nonaene
• CAS: 13920-14-4
• 化学式: C₄₀H₆₄
• 分子量: 544.948
• InChiKey: YVLPJIGOMTXXLP-BHLJUDRVSA-N

物化性质

• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  15.3
• 重原子数：
  40
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  7,7',8,8',11,11',12,12'-八氢-psi,psi-胡罗卜素 在 铂 作用下， 生成 2,6,10,14,19,23,27,31-八甲基三十二烷
  参考文献：
  名称：

  Rabourn; Quackenbush, Archives of Biochemistry, 1956, vol. 61, p. 111,112,116

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (E,E,E)-geranylgeranoate 在 1,2-环氧丁烷 、 lithium aluminium tetrahydride 、 silver carbonate 作用下， 以 乙醚 、 苯 为溶剂， 生成 7,7',8,8',11,11',12,12'-八氢-psi,psi-胡罗卜素
  参考文献：
  名称：

  Khan,N. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1457 - 1464

  摘要：

  DOI：

文献信息

• Expression of a Tomato cDNA Coding for Phytoene Synthase in Escherichia coli, Phytoene Formation In Vivo and In Vitro, and Functional Analysis of the Various Truncated Gene Products1
  作者：Norihiko Misawa、Mark R. Truesdale、Gerhard Sandmann、Paul D. Fraser、Colin Bird、Wolfgang Schuch、Peter M. Bramley

  DOI：10.1093/oxfordjournals.jbchem.a124656

  日期：1994.11

  Full length and truncated cDNA expression constructs of the phytoene synthase (psy) gene from tomato have been ligated into a pUC8 cloning vector. One of the truncated constructs was introduced into Escherichia coli carrying the Erwinia uredovora GGPP synthase gene. This transformant produced 15, 15' -cis-phytoene, which was identified on the basis of its UV and IR spectral data, from geranylgeranyl diphosphate. The function of this gene product was further confirmed by in vitro assay using cell-free extract of E. coli harboring the construct. On transformation with the above constructs together with a plasmid containing the carotenoid gene cluster from E. uredovora devoid of the phytoene synthase (crtB) gene, yellow, carotenoid-containing, E. coli colonies were produced. The amounts of carotenoids synthesized by the transformed cells, related to the steady-state levels of psy mRNA, varied depending upon the psy constructs. The full-length psy clone produced 16-fold less carotenoids per unit amount of RNA than cells containing phytoene synthase without the first 114 N-terminal amino acids. Removal of further amino acids from the N-terminus caused a large decrease in carotenogenesis. A Western blot of ripe fruit stroma with a monoclonal antibody raised against phytoene synthase revealed a single protein band of apparent molecular mass 38 kDa. Based upon this immunological evidence, we conclude that the size of the transit peptide of phytoene synthase from ripe tomato fruit is approximately 9 kDa, corresponding to about 80 amino acid residues. But removal of further N-terminal amino acids up to 114 from the enzyme, to yield a protein of apparent molecular mass 34 kDa, increases its catalytic activity in E. coli.

  番茄植物烯合成酶（psy）基因的全长和截短 cDNA 表达构建体被连接到 pUC8 克隆载体中。其中一个截短的构建体被导入携带 Erwinia uredovora GGPP 合成酶基因的大肠杆菌中。该转化子产生了 15，15' -顺式植物烯，根据其紫外和红外光谱数据，确定其来自于香叶基二磷酸。利用携带该构建体的大肠杆菌的无细胞提取物进行体外检测，进一步证实了该基因产物的功能。将上述构建体与含有来自 E. uredovora 的类胡萝卜素基因簇（没有植物烯合成酶（crtB）基因）的质粒一起转化后，产生了黄色的、含有类胡萝卜素的大肠杆菌菌落。转化细胞合成类胡萝卜素的量与 psy mRNA 的稳态水平有关，因 psy 构建体而异。与含有不含前 114 个 N 端氨基酸的植物烯合成酶的细胞相比，全长 psy 克隆每单位 RNA 量产生的类胡萝卜素少 16 倍。去除 N 端更多的氨基酸会导致类胡萝卜素生成量大幅下降。用针对植物烯合成酶的单克隆抗体对成熟果实基质进行 Western 印迹，发现一条明显分子质量为 38 kDa 的蛋白质条带。根据这一免疫学证据，我们得出结论，成熟番茄果实中植物烯合成酶的转运肽大小约为 9 kDa，相当于约 80 个氨基酸残基。但从酶中去除更多的 N 端氨基酸，直至 114 个氨基酸，得到表观分子质量为 34 kDa 的蛋白质，可提高其在大肠杆菌中的催化活性。
• A Single Five-Step Desaturase Is Involved in the Carotenoid Biosynthesis Pathway to β-Carotene and Torulene in Neurospora crassa
  作者：Alexander Hausmann、Gerhard Sandmann

  DOI：10.1006/fgbi.2000.1212

  日期：2000.7

  related bacterial enzymes, the cofactor involved in the dehydrogenation reaction was NAD for Al-1. In situ competition with a neurosporene- and lycopene-converting hydratase and cyclase indicated that these enzymes can divert intermediates of the desaturation sequence. Based on the in vitro and in vivo results, the organization of the phytoene desaturase from N. crassa was proposed as an assembly of identical

  在大肠杆菌中表达了来自神经孢霉的植物烯去饱和酶Al-1，并分离了一种活性酶，该酶催化了多达五个双键逐步引入底物八氢番茄红素中。主要反应产物是3，4-二氢番茄红素和番茄红素。Al-1还接受了几种去饱和中间体，ζ-胡萝卜素，神经孢子烯和番茄红素。与结构相关的细菌酶相反，参与脱氢反应的辅因子是Al-1的NAD。与转化神经孢子和番茄红素的水合酶和环化酶的原位竞争表明，这些酶可以转移去饱和序列的中间体。根据体外和体内结果，从N中组织八氢番茄红素去饱和酶。提出了crassa作为负责多步反应的相同蛋白质单元的组装。但是，空间布置应足够宽松，以允许单个中间体在进出该复合体的两个方向上进行交换。由于Al-1不接受γ-胡萝卜素作为底物，因此，甲苯的形成必须仅通过3,4-二氢番茄红素的环化来进行。
• Novel apocarotenoid intermediates in Neurospora crassa mutants imply a new biosynthetic reaction sequence leading to neurosporaxanthin formation
  作者：Alejandro F. Estrada、Dominic Maier、Daniel Scherzinger、Javier Avalos、Salim Al-Babili

  DOI：10.1016/j.fgb.2008.09.001

  日期：2008.11

  Neurosporaxanthin, beta-apo-4'-carotenoic acid (C35), represents the end-product of the carotenoid pathway in Neurospora crassa. It is supposed to be synthesized in three steps catalyzed by sequential AL-2, CAO-2 and YLO-1 activities: (i) cyclization of 3,4-didehydrolycopene (C40); (ii) cleavage of torulene into beta-apo-4'-carotenal (C35); and finally (iii) oxidation of beta-apo-4'-carotenal. However

  Neurosporaxanthin，β-apo-4'-胡萝卜酸（C35）代表了Neurospora crassa中类胡萝卜素途径的终产物。据推测，它是由连续的AL-2，CAO-2和YLO-1活性催化的三个步骤合成的：（i）3,4-二氢番茄红素（C40）的环化；（ii）将甲苯裂解为β-apo-4'-胡萝卜素（C35）；最后（iii）氧化β-apo-4'-胡萝卜素。但是，对ylo-1突变体的分析揭示了除β-apo-4'-胡萝卜素以外的中间体的积累。在这里，我们生成了一个3,4-二氢番茄红素积聚的大肠杆菌菌株，并表明CAO-2在体内和体外裂解了这种无环胡萝卜素，产生了apo-4'-lycopenal。然后将ylo-1突变体中积累的阿朴类胡萝卜素鉴定为apo-4'-lycopenal和apo-4'-lycopenol，指出前者是YLO-1底物，并表明环化是神经孢黄质生物合成的最后一步。通过分析缺乏
• Phytoene Desaturase: Heterologous Expression in an Active State, Purification, and Biochemical Properties
  作者：Christian Schneider、Peter Böger、Gerhard Sandmann

  DOI：10.1006/prep.1997.0730

  日期：1997.7

  Conditions were developed for heterologous expression in Escherichia coli of the membrane-bound cyanobacterial/plant-type phytoene desaturase (PDS) from Synechococcus in an active form. Decrease of growth temperature for the transformant to 28 degrees C resulted in an increase of proteins in a supernatant fraction obtained after pressure disruption (20 MPa) of cells and centrifugation. This supernatant

  为大肠杆菌中的膜结合蓝细菌/植物型八氢番茄红素去饱和酶（PDS）以活性形式在异源表达中开发了条件。转化子的生长温度降低到28摄氏度，导致细胞压力破坏（20 MPa）和离心后获得的上清液级分中的蛋白质增加。发现其中PDS活性最高的上清液用于通过硫酸铵沉淀和DEAE色谱法纯化为均质蛋白。纯化的PDS用于确定底物特异性和辅因子需求。除八氢番茄红素以外的底物是八氢番茄红素和1，2-环氧八氢番茄红素，它们被转化为ζ-胡萝卜素和相应的1，2-环氧。NAD，NADP和氧气刺激反应。
• Purification in an Active State and Properties of the 3-Step Phytoene Desaturase from Rhodobacter capsulatus Overexpressed in Escherichia coil
  作者：A. Raisig、G. Bartley、P. Scolnik、G. Sandmann

  DOI：10.1093/oxfordjournals.jbchem.a021278

  日期：1996.3.1

  product formation. In addition to phytoene, the intermediates, phytofluene and zeta-carotene, were both converted to neurosporene, the end product of the reaction. Furthermore, 1,2-epoxy phytoene was a suitable substrate whereas the C30 diapophytoene was not. The Km values for phytoene and zeta-carotene were determined to be 33.3 and 16.6 microM, respectively. The desaturation reaction is dependent on the

  来自荚膜红细菌的八氢番茄红素去饱和酶基因在大肠杆菌中表达，并纯化得到的蛋白质。涉及的纯化步骤是硫酸铵沉淀和离子交换色谱法，得到具有高比酶活性的57 kDa的均质蛋白。关于底物特异性和产物形成对纯化的酶进行表征。除了八氢番茄红素，中间体，八氢番茄红素和ζ-胡萝卜素都被转化为神经孢子烯，这是反应的最终产物。此外，1,2-环氧八氢番茄红素是合适的底物，而C30二氢番茄红素不是合适的底物。测出的六氢番茄红素和ζ-胡萝卜素的Km值分别为33.3和16.6 microM。脱饱和反应取决于辅因子FAD。氧化的烟碱核苷酸或ATP没有积极作用。FAD的Km值为4.9 microM。用二苯胺观察到了去饱和反应的抑制。