delta-carotene | 472-92-4

• 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
• 英文名称: delta-carotene
• 英文别名: (all-E)-ε,ψ-Carotin；δ-carotene；δ-Carotin；delta carotene；(+/-)-δ-Carotin；epsilon,psi-Carotene；6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E,19E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,23-undecaenyl]-1,5,5-trimethylcyclohexene
• CAS: 472-92-4
• 化学式: C₄₀H₅₆
• 分子量: 536.885
• InChiKey: WGIYGODPCLMGQH-BXOLYSJBSA-N

物化性质

• 熔点：
  140.5°
• 比旋光度：
  Cd +317°; D25 +352° ±16% (hexane)
• 沸点：
  648.1±45.0 °C(Predicted)
• 密度：
  0.911±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  delta-carotene 生成 epsilon-carotene
  参考文献：
  名称：

  One ring or two? Determination of ring number in carotenoids by lycopene ɛ-cyclases

  摘要：

  植物光合膜中的类胡萝卜素通常包含两个β-环（例如β-胡萝卜素和玉米黄质）或一个ɛ-环和一个β-环（例如叶黄素）。具有两个ɛ-环的类胡萝卜素很少见。我们之前报道过拟南芥番茄红素ɛ-环化酶（LCYe）将对称线性底物番茄红素加入一个ɛ-环，而结构相关的番茄红素β-环化酶（LCYb）则加入两个β-环。在这里，我们描述了罗曼生菜（Lactuca sativa var. romaine）中编码LCYe的cDNA，罗曼生菜是为数不多的已知积累大量具有两个ɛ-环的类胡萝卜素（lactucaxanthin）的植物物种之一。与拟南芥LCYe相似的产物（77％氨基酸同源性）有效地将番茄红素转化为双环ɛ-胡萝卜素，在异源大肠杆菌系统中。通过使用反向PCR方法构建的嵌合ɛ-环化酶的分析，映射了罗曼生菜和拟南芥ɛ-环化酶中决定环数的区域。发现单个氨基酸作为分子开关：罗曼生菜LCYe突变体H457L仅向番茄红素添加一个ɛ-环，而互补的拟南芥LCYe突变体L448H添加两个ɛ-环。该位置的R残基也为罗曼生菜和拟南芥酶产生双ɛ-环化酶。构建和分析具有不同催化活性的相关酶的嵌合体，提供了一种有益的方法，特别适用于研究不能轻易结晶或建模到现有晶体结构的膜相关酶。

  DOI：

  10.1073/pnas.051618398
• 作为产物：
  描述：

  γ-retinal 在 manganese(IV) oxide 、 氢氧化钾 、 sodium methylate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 delta-carotene
  参考文献：
  名称：

  合成胡萝卜素-端基和（Z）-修饰末端的多巴宾登根

  摘要：

  末端共轭双键具有ψ-端基和（Z）-构型的胡萝卜素的合成

  DOI：

  10.1002/hlca.19850680604

文献信息

• One ring or two? Determination of ring number in carotenoids by lycopene ɛ-cyclases
  作者：Francis X. Cunningham、Elisabeth Gantt

  DOI：10.1073/pnas.051618398

  日期：2001.2.27

  Carotenoids in the photosynthetic membranes of plants typically contain two β-rings (e.g., β-carotene and zeaxanthin) or one ɛ- and one β-ring (e.g., lutein). Carotenoids with two ɛ-rings are uncommon. We reported earlier that the Arabidopsis thaliana lycopene ɛ-cyclase (LCYe) adds one ɛ-ring to the symmetrical linear substrate lycopene, whereas the structurally related lycopene β-cyclase (LCYb) adds two β-rings. Here we describe a cDNA encoding LCYe in romaine lettuce ( Lactuca sativa var. romaine), one of the few plant species known to accumulate substantial quantities of a carotenoid with two ɛ-rings: lactucaxanthin. The product of the lettuce cDNA, similar in sequence to the Arabidopsis LCYe (77% amino acid identity), efficiently converted lycopene into the bicyclic ɛ-carotene in a heterologous Escherichia coli system. Regions of the lettuce and Arabidopsis ɛ-cyclases involved in the determination of ring number were mapped by analysis of chimeric ɛ-cyclases constructed by using an inverse PCR approach. A single amino acid was found to act as a molecular switch: lettuce LCYe mutant H457L added only one ɛ-ring to lycopene, whereas the complementary Arabidopsis LCYe mutant, L448H, added two ɛ-rings. An R residue in this position also yields a bi-ɛ-cyclase for both the lettuce and Arabidopsis enzymes. Construction and analysis of chimera of related enzymes with differing catalytic activities provide an informative approach that may be of particular utility for studying membrane-associated enzymes that cannot easily be crystallized or modeled to existing crystal structures.

  植物光合膜中的类胡萝卜素通常包含两个β-环（例如β-胡萝卜素和玉米黄质）或一个ɛ-环和一个β-环（例如叶黄素）。具有两个ɛ-环的类胡萝卜素很少见。我们之前报道过拟南芥番茄红素ɛ-环化酶（LCYe）将对称线性底物番茄红素加入一个ɛ-环，而结构相关的番茄红素β-环化酶（LCYb）则加入两个β-环。在这里，我们描述了罗曼生菜（Lactuca sativa var. romaine）中编码LCYe的cDNA，罗曼生菜是为数不多的已知积累大量具有两个ɛ-环的类胡萝卜素（lactucaxanthin）的植物物种之一。与拟南芥LCYe相似的产物（77％氨基酸同源性）有效地将番茄红素转化为双环ɛ-胡萝卜素，在异源大肠杆菌系统中。通过使用反向PCR方法构建的嵌合ɛ-环化酶的分析，映射了罗曼生菜和拟南芥ɛ-环化酶中决定环数的区域。发现单个氨基酸作为分子开关：罗曼生菜LCYe突变体H457L仅向番茄红素添加一个ɛ-环，而互补的拟南芥LCYe突变体L448H添加两个ɛ-环。该位置的R残基也为罗曼生菜和拟南芥酶产生双ɛ-环化酶。构建和分析具有不同催化活性的相关酶的嵌合体，提供了一种有益的方法，特别适用于研究不能轻易结晶或建模到现有晶体结构的膜相关酶。
• 360. Carotenoids and related compounds. Part XI. Syntheses of δ-carotene and ε-carotene
  作者：P. S. Manchand、R. Rüegg、U. Schwieter、P. T. Siddons、B. C. L. Weedon

  DOI：10.1039/jr9650002019

  日期：——
• Synthesen von Carotinen mit ?-Endgruppen und (Z)-Konfiguration an terminalen konjugierten Doppelbindungen
  作者：Albrecht Zumbrunn、Peter Uebelhart、Conrad Hans Eugster

  DOI：10.1002/hlca.19850680604

  日期：1985.9.25

  Syntheses of Carotenes with ψ-End Groups and (Z)-Configuration at Terminal Conjugated Double Bonds

  末端共轭双键具有ψ-端基和（Z）-构型的胡萝卜素的合成
• A novel type of lycopene ε-cyclase in the marine cyanobacterium Prochlorococcus marinus MED4
  作者：Per Stickforth、Sabine Steiger、Wolfgang R. Hess、Gerhard Sandmann

  DOI：10.1007/s00203-003-0545-4

  日期：2003.6

  Chlorophyll-b-possessing cyanobacteria of the genus Prochlorococcus share the presence of high amounts of alpha- and beta-carotenoids with green algae and higher plants. The branch point in carotenoid biosynthesis is the cyclization of lycopene, for which in higher plants two distinct enzymes are required, epsilon- and beta-lycopene cyclase. All cyanobacteria studied so far possess a single beta-cyclase. Here, two different Prochlorococcus sp. MED4 genes were functionally identified by heterologous gene complementation in Escherichia coli to encode lycopene cyclases. Whereas one is both functionally and in sequence highly similar to the beta-cyclase of Synechococcus sp. strain PCC 7942 and other cyanobacteria, the other showed several intriguing features. It acts as a bifunctional enzyme catalyzing the formation of epsilon- as well as of beta-ionone end groups. Expression of this cyclase in E. coli resulted in the simultaneous accumulation of alpha- beta-, delta-, and epsilon-carotene. Such an activity is in contrast to all lycopene epsilon-cyclases known so far, including those of the higher plants. Thus, for the first time among prokaryotes, two individual enzymes were identified in one organism that are responsible for the formation of cyclic carotenoids with either beta- or epsilon-end groups. These two genes are suggested to be designated as crtL-b and crtL-e. The results indicate that both enzymes might have originated from duplication of a single gene. Consequently, we suggest that multiple gene duplications followed by functional diversification resulted several times, and in independent lineages, in the appearance of enzymes for the biosynthesis of cyclic carotenoids.