(3S,3'R)-3,3'-dihydroxy-β,β-caroten-4-one | 4418-73-9

• 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: (3S,3'R)-3,3'-dihydroxy-β,β-caroten-4-one
• 英文别名: (3S,3'R)-4-ketozeaxanthin；(3S, 3'R)-Adonixanthin；(3S,3'R)-Adonixanthin；trans-adonixanthin；adonixanthin；(6S)-6-hydroxy-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethylcyclohex-2-en-1-one
• CAS: 4418-73-9
• 化学式: C₄₀H₅₄O₃
• 分子量: 582.867
• InChiKey: YECXHLPYMXGEBI-ZNQVSPAOSA-N

物化性质

• 沸点：
  742.2±60.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  AH₂ 、 (3S,3'R)-3,3'-dihydroxy-β,β-caroten-4-one 、 氧气 生成 A 、 虾青素 、 水
  参考文献：
  名称：

  Functional characterization of various algal carotenoid ketolases reveals that ketolating zeaxanthin efficiently is essential for high production of astaxanthin in transgenic Arabidopsis

  摘要：

  将类胡萝卜素途径扩展到植物中的虾青素，具有重要的科学和工业意义。然而，在转基因植物中，催化酮类胡萝卜素形成的微生物β-胡萝卜素酮化酶（BKT）的表达通常会导致虾青素含量较低。BKT将玉米黄质转化为虾青素的效率较低，这被认为是工程植物中虾青素积累的主要限制因素。为了验证这一假设，研究人员使用大肠杆菌系统对几种藻类BKT的功能进行了表征，并鉴定出三种BKT，它们分别具有高（高达85%）、中等（约38%）和低（约1%）的玉米黄质向虾青素转化率，分别来自萊茵衣藻（CrBKT）、小球藻（CzBKT）和雨生红球藻（HpBKT3）。表达CrBKT的转基因拟南��

  DOI：

  10.1093/jxb/err070
• 作为产物：
  描述：

  2,7-二甲基-2,4,6-辛三烯二醛 在 盐酸 、 硫酸 、 sodium methylate 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 17.53h， 生成 (3S,3'R)-3,3'-dihydroxy-β,β-caroten-4-one
  参考文献：
  名称：

  合成胡萝卜素，天然胡萝卜素和天然维生素。九。合成冯（3 - [R）-Hydroxyechinenon，（3 - [R，3' - [R） - UND（3 - [R，3'小号）-Adonixanthin，（3 - [R）-Adonirubin，得润optischen Antipoden UND verwandten Verbindungen †

  摘要：

  光学活性天然类胡萝卜素和结构相关化合物的合成。九。（3的合成[R）-Hydroxyechinenone，（3 - [R，3' - [R ）-和（3 - [R，3'小号）-Adonixanthin，（3 - [R）-Adonirubin，其旋光对映和相关化合物

  DOI：

  10.1002/hlca.19810640754

文献信息

• Functional characterization of various algal carotenoid ketolases reveals that ketolating zeaxanthin efficiently is essential for high production of astaxanthin in transgenic Arabidopsis
  作者：Y.-J. Zhong、J.-C. Huang、J. Liu、Y. Li、Y. Jiang、Z.-F. Xu、G. Sandmann、F. Chen

  DOI：10.1093/jxb/err070

  日期：2011.6.1

  Extending the carotenoid pathway to astaxanthin in plants is of scientific and industrial interest. However, expression of a microbial β-carotene ketolase (BKT) that catalyses the formation of ketocarotenoids in transgenic plants typically results in low levels of astaxanthin. The low efficiency of BKTs in ketolating zeaxanthin to astaxanthin is proposed to be the major limitation for astaxanthin accumulation in engineered plants. To verify this hypothesis, several algal BKTs were functionally characterized using an Escherichia coli system and three BKTs were identified, with high (up to 85%), moderate (∼38%), and low (∼1%) conversion rate from zeaxanthin to astaxanthin from Chlamydomonas reinhardtii (CrBKT), Chlorella zofingiensis (CzBKT), and Haematococcus pluvialis (HpBKT3), respectively. Transgenic Arabidopsis thaliana expressing the CrBKT developed orange leaves which accumulated astaxanthin up to 2 mg g−1 dry weight with a 1.8-fold increase in total carotenoids. In contrast, the expression of CzBKT resulted in much lower astaxanthin content (0.24 mg g−1 dry weight), whereas HpBKT3 was unable to mediate synthesis of astaxanthin in A. thaliana. The none-native astaxanthin was found mostly in a free form integrated into the light-harvesting complexes of photosystem II in young leaves but in esterified forms in senescent leaves. The alteration of carotenoids did not affect chlorophyll content, plant growth, or development significantly. The astaxanthin-producing plants were more tolerant to high light as shown by reduced lipid peroxidation. This study advances a decisive step towards the utilization of plants for the production of high-value astaxanthin.

  将类胡萝卜素途径扩展到植物中的虾青素，具有重要的科学和工业意义。然而，在转基因植物中，催化酮类胡萝卜素形成的微生物β-胡萝卜素酮化酶（BKT）的表达通常会导致虾青素含量较低。BKT将玉米黄质转化为虾青素的效率较低，这被认为是工程植物中虾青素积累的主要限制因素。为了验证这一假设，研究人员使用大肠杆菌系统对几种藻类BKT的功能进行了表征，并鉴定出三种BKT，它们分别具有高（高达85%）、中等（约38%）和低（约1%）的玉米黄质向虾青素转化率，分别来自萊茵衣藻（CrBKT）、小球藻（CzBKT）和雨生红球藻（HpBKT3）。表达CrBKT的转基因拟南��
• Novel carotenoid hydroxylase gene, method for preparing hydroxylated carotenoid, and novel geranylgeranyl pyrophosphate synthase
  申请人：Nishida Yasuhiro

  公开号：US20070148727A1

  公开（公告）日：2007-06-28

  The present invention provides a Brevundimonas sp. strain SD212-derived peptide having β-ionone ring-2-hydroxylase activity and a gene encoding the same, to thereby make it possible to produce rare carotenoids in which a hydroxyl group is introduced at the position 2 (2′) carbon in their β-ionone ring in large quantities. The present invention also provides a novel gene encoding an enzyme which introduces a hydroxyl group at the position 3 (3′) carbon in the β-ionone ring of carotenoids, and a novel gene encoding a geranylgeranyl pyrophosphate synthase.
• Synthese von optisch aktiven, natürlichen Carotinoiden und strukturell verwandten Naturprodukten. IX. Synthese von (3<i>R</i>)-Hydroxyechinenon, (3<i>R</i>, 3′<i>R</i>)- und (3<i>R</i>, 3′<i>S</i>)-Adonixanthin, (3<i>R</i>)-Adonirubin, deren optischen Antipoden und verwandten Verbindungen
  作者：Kurt Bernhard、Gerhard Englert、Hans Mayer、Robert K. Müller、August Rüttimann、Max Vecchi、Erich Widmer、Reinhard Zell

  DOI：10.1002/hlca.19810640754

  日期：1981.11.4

  Synthesis of Optically Active Natural Carotenoids and Structurally Related Compounds. IX. Synthesis of (3R)-Hydroxyechinenone, (3R, 3′R)- and (3R, 3′S)-Adonixanthin, (3R)-Adonirubin, Their Optical Antipodes and Related Compounds

  光学活性天然类胡萝卜素和结构相关化合物的合成。九。（3的合成[R）-Hydroxyechinenone，（3 - [R，3' - [R ）-和（3 - [R，3'小号）-Adonixanthin，（3 - [R）-Adonirubin，其旋光对映和相关化合物
• Cloning and selection of carotenoid ketolase genes for the engineering of high-yield astaxanthin in plants
  作者：Junchao Huang、Yujuan Zhong、Gerhard Sandmann、Jin Liu、Feng Chen

  DOI：10.1007/s00425-012-1654-6

  日期：2012.8

  beta-Carotene ketolase (BKT) catalyzes the rate-limiting steps for the biosynthesis of astaxanthin. Several bkt genes have been isolated and explored to modify plant carotenoids to astaxanthin with limited success. In this study, five algal BKT cDNAs were isolated and characterized for the engineering of high-yield astaxanthin in plants. The products of the cDNAs showed high similarity in sequence and enzymatic activity of converting beta-carotene into canthaxanthin. However, the enzymes exhibited extremely different activities in converting zeaxanthin into astaxanthin. Chlamydomonas reinhardtii BKT showed the highest conversion rate (ca 85 %), whereas, Neochloris wimmeri BKT exhibited very poor activity of ketolating zeaxanthin. Expression of C. reinhardtii BKT in tobacco led to a twofold increase of total carotenoids in the leaves with astaxanthin being the predominant. The bkt genes described here provide a valuable resource for metabolic engineering of plants as cell factories for astaxanthin production.