(-)-(R)-all-trans-3-hydroxyretinal | 60046-53-9

• 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: (-)-(R)-all-trans-3-hydroxyretinal
• 英文别名: all-trans-(3R)-3-Hydroxyretinal；3R-hydroxy-all-trans-retinal；apo-15-zeaxanthinal；3-OH-β-apo-15-carotenal；3-hydroxyretinal；3-OH-retinal；(3R)-all-trans-3-hydroxyretinal；(2E,4E,6E,8E)-9-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenal
• CAS: 60046-53-9
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: QPRQNCDEPWLQRO-ZCEAMUHZSA-N

物化性质

• 沸点：
  462.3±28.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  glyoxalic acid 2,4,6-trisopropylphenylsulfonylhydrazone 、 (-)-(R)-all-trans-3-hydroxyretinal 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 3R-diazoacetoxy-all-trans-retinal
  参考文献：
  名称：

  Synthesis of optically active 3-diazoacetylretinals with triisopropylphenylsulfonylhydrazone

  摘要：

  DOI：

  10.1016/s0040-4039(00)86036-0
• 作为产物：
  描述：

  (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene 在 tris(dibenzylideneacetone)dipalladium (0) N,N-二甲基丙烯基脲 、 manganese(IV) oxide 、 正丁基锂 、 四丙基高钌酸铵 、 三苯胂 、 4 A molecular sieve 、 四丁基氟化铵 、 二异丁基氢化铝 、 sodium carbonate 、 N-甲基吗啉氧化物 、 lithium chloride 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 正己烷 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 (-)-(R)-all-trans-3-hydroxyretinal
  参考文献：
  名称：

  Synthesis of enantiopure C₃- and C₄-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis

  摘要：

  (R)-全反式-3-羟基视黄醛 1、(S)-全反式-4-羟基视黄醛 3 和(R)-全反式-4-羟基视黄醛 5 是通过 Horner-Wadsworth-Emmons 和 Stille 交叉偶联作为成键反应立体选择性合成的。在对映体分离步骤中采用了 CBS 酮还原法，为 4-羟基视黄醛对映体的合成提供了前体。已测定了爪蟾 ADH8 与这些视黄酸的动力学常数。

  DOI：

  10.1039/b514273c

文献信息

• Optically active cyclohexane derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US04026949A1

  公开（公告）日：1977-05-31

  A process for fermentatively hydrogenating and reducing ketoisophorone to produce optically active [4R,6R]-4-hydroxy-2,6,6-trimethyl-cyclohexanone useful as an intermediate in the production of optically active carotenoids and intermediates in the production of these carotenoids.

  一种通过发酵氢化和还原酮异福酮的方法，生产出具有光学活性的[4R,6R]-4-羟基-2,6,6-三甲基环己酮，可用作生产光学活性类胡萝卜素和这些类胡萝卜素的中间体的中间体。
• The Mycobacterium tuberculosis ORF Rv0654 encodes a carotenoid oxygenase mediating central and excentric cleavage of conventional and aromatic carotenoids
  作者：Daniel Scherzinger、Erdmann Scheffer、Cornelia Bär、Hansgeorg Ernst、Salim Al-Babili

  DOI：10.1111/j.1742-4658.2010.07873.x

  日期：2010.11

  acid, is initiated by the β‐carotene cleavage oxygenases I and II catalyzing either a central or an excentric cleavage of β‐carotene, respectively. The M. tuberculosis ORF Rv0654 codes for a putative carotenoid oxygenase conserved in other mycobacteria. In the present study, we investigated the corresponding enzyme, here named M. tuberculosis carotenoid cleavage oxygenase (MtCCO). Using heterologously

  结核分枝杆菌是结核的病原体，被认为缺乏类胡萝卜素，类胡萝卜素是广泛存在的色素，具有重要的功能，可作为自由基清除剂和类胡萝卜素的来源。在哺乳动物中，包括视黄酸在内的类胡萝卜素的合成是由β-胡萝卜素裂解加氧酶I和II分别催化β-胡萝卜素的中心裂解或偏心裂解引起的。在结核分枝杆菌ORF Rv0654编码推定的类胡萝卜素氧保守在其它分枝杆菌。在本研究中，我们研究了相应的酶，在这里称为结核分枝杆菌类胡萝卜素裂解加氧酶（MtCCO）。使用异源表达和纯化的蛋白质，我们表明MtCCO在体外可转化几种类胡萝卜素和类胡萝卜素。此外，产品鉴定表明，与其他类胡萝卜素加氧酶不同，MtCCO裂解中央C15-C15'和C13-C14位置的偏心双键，从而导致视网膜（C 20），β-​​载脂蛋白14 '-胡萝卜素（C 22）和β-载脂蛋白13-胡萝卜素（C 18）和β-胡萝卜素的相应羟基化产物，以及玉米黄质和叶黄素的相应羟基化产物。此外，该酶还切割3
• Synthese von optisch aktiven, natürlichen Carotinoiden und strukturell verwandten Naturprodukten. VII. Synthese von (3<i>R</i>)-3-Hydroxyretinol, (3<i>R</i>)-3-Hydroxyretinal und (3<i>R</i>)-3-Hydroxyretinsäure
  作者：Hans Mayer、Jean-Marie Santer

  DOI：10.1002/hlca.19800630617

  日期：1980.9.17

  Synthesis of optically active natural carotenoids and structurally related compounds. VII. Synthesis of (3R)-3-hydroxyretinol, (3R)-3-hydroxyretinal and (3R)-3-hydroxyretinoic acid

  光学活性天然类胡萝卜素和结构相关化合物的合成。七。（3的合成[R）-3- hydroxyretinol，（3 - [R）-3- hydroxyretinal和（3 - [R）-3- hydroxyretinoic酸
• NinaB combines carotenoid oxygenase and retinoid isomerase activity in a single polypeptide
  作者：Vitus Oberhauser、Olaf Voolstra、Annette Bangert、Johannes von Lintig、Klaus Vogt

  DOI：10.1073/pnas.0807805105

  日期：2008.12.2

  In animals, successful production of the visual chromophore (11- cis -retinal or derivatives thereof such as 11- cis -3-hydroxy-retinal) is essential for photoreceptor cell function and survival. These carotenoid-derived compounds must combine with a protein moiety (the opsin) to establish functional visual pigments. Evidence from cell culture systems has implicated that the retinal pigment epithelium protein of 65 kDa (RPE65) is the long-sought all- trans to 11- cis retinoid isomerase. RPE65 is structurally related to nonheme iron oxygenases that catalyze the conversion of carotenoids into retinoids. In vertebrate genomes, two carotenoid oxygenases and RPE65 are encoded, whereas in insect genomes only a single representative of this protein family, named NinaB (denoting neither inactivation nor afterpotential mutant B), is encoded. We here cloned and functionally characterized the ninaB gene from the great wax moth Galleria mellonella . We show that the recombinant purified enzyme combines isomerase and oxygenase (isomerooxygenase) activity in a single polypeptide. From kinetics and isomeric composition of cleavage products of asymmetrical carotenoid substrates, we propose a model for the spatial arrangement between substrate and enzyme. In Drosophila , we show that carotenoid-isomerooxygenase activity of NinaB is more generally found in insects, and we provide physiological evidence that carotenoids such as 11- cis -retinal can promote visual pigment biogenesis in the dark. Our study demonstrates that trans/cis isomerase activity can be intrinsic to this class of proteins and establishes these enzymes as key components for both invertebrate and vertebrate vision.

  在动物中，成功生成视觉色素（11-cis-视黄醛或其衍生物，如11-cis-3-羟基-视黄醛）对于光感受器细胞的功能和存活至关重要。这些来源于类胡萝卜素的化合物必须与蛋白质基团（视蛋白）结合，以建立功能性的视觉色素。细胞培养系统的证据表明，65 kDa的视网膜色素上皮蛋白（RPE65）是长期寻求的全反式到11-顺式视黄醛异构酶。RPE65在结构上与催化类胡萝卜素转化为视黄醇的非血红素铁氧化酶相关。在脊椎动物基因组中，编码两种类胡萝卜素氧化酶和RPE65，而在昆虫基因组中仅编码该蛋白家族的单个代表，称为NinaB（表示无失活或潜伏突变体B）。我们在大蜡螟Galleria mellonella中克隆并功能性地表征了ninaB基因。我们展示了重组纯化酶在单个多肽中结合异构酶和氧化酶（异构氧化酶）活性。通过不对称类胡萝卜素底物的裂解产物的动力学和异构构成，我们提出了底物和酶之间的空间排列模型。在果蝇中，我们展示了NinaB的类胡萝卜素异构氧化酶活性更普遍地在昆虫中发现，并提供了生理学证据表明，如11-cis-视黄醛等类胡萝卜素可以促进暗处视觉色素的生物合成。我们的研究表明，全反/顺异构酶活性可以是这类蛋白质的内在特性，并将这些酶建立为无脊椎动物和脊椎动物视觉的关键组成部分。
• Filling the Gap in Vitamin A Research
  作者：Johannes von Lintig、Klaus Vogt

  DOI：10.1074/jbc.275.16.11915

  日期：2000.4

  Vitamin A and its derivatives (retinoids) are essential components in vision; they contribute to pattern formation during development and exert multiple effects on cell differentiation with important clinical implications. It has been known for 50 years that the key step in the formation of vitamin A is the oxidative cleavage of beta-carotene; however, this enzymatic step has resisted molecular analysis. A novel approach enabled us to clone and identify a beta-carotene dioxygenase from Drosophila melanogaster, expressing it into the background of a beta-carotene (provitamin A)-synthesizing and -accumulating Escherichia coli strain. The carotene-cleaving enzyme, identified here for the first time on the molecular level, is the basis of the numerous branches of vitamin A action and links plant and animal carotene metabolism.