vestitone | 158112-50-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: vestitone
• 英文别名: vestitol；(3R)-vestitol；(3R)-7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 158112-50-6
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: WQCJOKYOIJVEFN-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  vestitone 、 NADP⁺ 生成 2'-Hydroxyformononetin(1-) 、 氢(+1)阳离子 、 NADPH(4-)
  参考文献：
  名称：

  Crystal Structure of Isoflavone Reductase from Alfalfa (Medicago sativa L.)

  摘要：

  Isoflavonoids play important roles in plant defense and exhibit a range of mammalian health-promoting activities. Isoflavone reductase (IFR) specifically recognizes isoflavones and catalyzes a stereospecific NADPH-dependent reduction to (3R)-isoflavanone. The crystal structure of Medicago sativa IFR with deletion of residues 39-47 has been determined at 1.6A resolution. Structural analysis, molecular modeling and docking, and comparison with the structures of other NADPH-dependent enzymes, defined the putative binding sites for co-factor and substrate and potential key residues for enzyme activity and substrate specificity. Further mutagenesis has confirmed the role of Lys144 as a catalytic residue. This study provides a structural basis for understanding the enzymatic mechanism and substrate specificity of IFRs as well as the functions of IFR-like proteins.

  DOI：

  10.1016/j.jmb.2006.03.022
• 作为产物：
  描述：

  (3R,4R)-7,2'-dihydroxy-4'-methoxyisoflavanol 、 NADP⁺ 生成 vestitone 、 氢(+1)阳离子 、 NADPH(4-)
  参考文献：
  名称：

  苜蓿（Medicago sativa L.）的类固醇激素还原酶的晶体结构。

  摘要：

  异黄酮通常在豆科植物中发现，它们在植物防御中起着重要作用，并且对动物和人类具有重大的健康益处。雌激素还原酶催化抗菌异黄酮类植物抗毒素麦地卡宾的生物合成中立体定向NADPH依赖性的（3R）-vestitone还原。紫花苜蓿（Medicago sativa L.）维甲酸酮还原酶的晶体结构已确定为1.4 A分辨率。该结构在N端包含一个经典的Rossmann折叠结构域和一个小的C端结构域。序列和结构分析表明，尽管序列同一性水平低，并且与具有已知结构的其他SDR酶相比，显着的结构差异，但维甲酸还原酶是短链脱氢酶/还原酶（SDR）超家族的成员。定义了辅助因子NADPH和底物（3R）-vestitone的假定结合位点，并位于酶N端和C端结构域之间形成的大裂口中。还确定了酶活性的潜在关键残基，包括催化三联体Ser129-Tyr164-Lys168。分子对接研究表明（3R）-香体酮而不是（3S）异构体与辅因

  DOI：

  10.1016/j.jmb.2007.03.040

文献信息

• [EN] BIOLOGICAL FERMENTATION USING DIHYDROXYACETONE AS A SOURCE OF CARBON<br/>[FR] FERMENTATION BIOLOGIQUE UTILISANT DE LA DIHYDROXYACÉTONE COMME SOURCE DE CARBONE
  申请人：KEMBIOTIX LLC

  公开号：WO2017139420A1

  公开（公告）日：2017-08-17

  The present invention relates to the use of hydrocarbons derived from natural gas in the fermentative production of biochemicals including biofuels. More specifically, the present invention provides the method for manufacturing dihydroxyacetone ("DHA") from natural gas, biogas, biomass and CO2 released from industrial plants including electricity-generating plants, steel mills and cement factories and the use of DHA as a source of organic carbon in the fermentative production of biochemicals including biofuels. The present invention comprises three stages. In the first stage of the present invention, syngas and formaldehyde are produced from natural gas, biogas, biomass and CO2 released from industrial plants. In the second stage of the present invention, formaldehyde and syngas are condensed to produce DHA. In the third stage of the present invention, biochemicals including biofuels are produced from DHA using fermentation process involving wild type or genetically modified microbial biocatalysts.

  本发明涉及使用从天然气中提取的碳氢化合物在生物化学品，包括生物燃料的发酵生产中的应用。更具体地说，本发明提供了一种从天然气、沼气、生物质和工业厂房中释放的CO2中制造二羟基丙酮（"DHA"）的方法，以及将DHA作为有机碳源在发酵生产中制造生物化学品，包括生物燃料的应用。本发明包括三个阶段。在本发明的第一阶段中，从天然气、沼气、生物质和工业厂房中释放的 中产生合成气和甲醛。在本发明的第二阶段中，甲醛和合成气被凝结成DHA。在本发明的第三阶段中，使用野生型或基因改造的微生物生物催化剂进行发酵过程，从DHA中生产生物化学品，包括生物燃料。
• Polynucleotide encoding 2-hydorxyisoflavanone dehydratase and application of the same
  申请人：Ayabe Shinichi

  公开号：US20070050865A1

  公开（公告）日：2007-03-01

  2-Hydroxyisoflavanone dehydratase substantially having the amino acid sequence represented by SEQ ID NO: 1 is isolated from licorice. Further, a polynucleotide encoding 2-hydroxyisoflavanone dehydratase of the SEQ ID NO: 2 is obtained. Furthermore, the amino acid sequence of 2-hydroxyisoflavanone dehydratase is identified from soybean and a polynucleotide encoding 2-hydroxyisoflavanone dehydratase is obtained.

  2-羟基异黄酮酮脱水酶，其氨基酸序列主要由SEQ ID NO: 1表示，从甘草中分离出来。此外，获得了编码SEQ ID NO: 2的2-羟基异黄酮酮脱水酶的多核苷酸。此外，从大豆中鉴定出2-羟基异黄酮酮脱水酶的氨基酸序列，并获得了编码2-羟基异黄酮酮脱水酶的多核苷酸。
• Molecular cloning and expression of alfalfa (Medicago sativa L.) vestitone reductase, the penultimate enzyme in medicarpin biosynthesis
  作者：Lining Guo、Nancy L. Paiva

  DOI：10.1016/0003-9861(95)90019-5

  日期：1995.7

  Medicarpin, the major phytoalexin in alfalfa, is synthesized by way of the isoflavonoid branch of phenylpropanoid metabolism. One of the final steps of medicarpin biosynthesis, from vestitone to 7,2'-dihydroxy-4'-methoxyisoflavanol, is catalyzed by vestitone reductase. A 1245-bp cDNA clone which encodes vestitone reductase was identified utilizing internal amino acid sequence of purified vestitone

  紫花苜蓿是苜蓿中的主要植物抗毒素，是通过苯丙烷代谢的异黄酮分支合成的。从卡比特酮到7，2'-二羟基-4'-甲氧基异黄烷醇的木果皮生物合成的最后步骤之一是由卡比特酮还原酶催化的。利用纯化的维甲酸还原酶的内部氨基酸序列鉴定出编码维甲酸还原酶的1245-bp cDNA克隆。当在大肠杆菌中表达时，克隆的酶对（3R）-vestitone表现出严格的底物立体定向性，正如从苜蓿中纯化的维甲酸还原酶所观察到的那样。蛋白质的计算分子量（35,918）与紫花苜蓿中纯化的海葵酮还原酶的分子量（通过SDS-PAGE测定为38 kDa）相似。维生素原还原酶转录水平（1。35kb）在添加苜蓿细胞悬浮培养物后的2小时内大大增加，而后归因还原酶活性和麦卡必丁生物合成迅速增加。在健康的苜蓿植物中，在根和根瘤中检测到最高水平的转录本，这与在这些组织中合成麦地卡宾及其结合物一致。脱水雌激素还原酶基因的克隆为研究和操纵豆类中的罗汉松生物合成提供了一种特定的工具。
• The ‘pterocarpan synthase” of alfalfa: Association and co-induction of vestitone reductase and 7,2′-dihydroxy-4′-methoxy-isoflavanol (DMI) dehydratase, the two final enzymes in medicarpin biosynthesis
  作者：Lining Guo、Richard A. Dixon、Nancy L. Paiva

  DOI：10.1016/0014-5793(94)01267-9

  日期：1994.12.19

  are the two final enzymes in medicarpin biosynthesis in alfalfa (Medicago sativa). Although two independent enzymes, vestitone reductase and DMI dehydratase can be loosely associated in low ionic strength buffers, presumably by a weak protein—protein interaction. The activities of vestitone reductase and DMI dehydratase increased approximately 3‐fold 6 hours after elicitor treatment in alfalfa suspension

  Vestetone 还原酶和 7,2'-二羟基-4'-甲氧基-异黄烷醇 (DMI) 脱水酶是苜蓿 (Medicago sativa) 中药卡平生物合成的两种最终酶。尽管两种独立的酶，vestitone 还原酶和 DMI 脱水酶可以在低离子强度缓冲液中松散地关联，大概是通过弱蛋白质 - 蛋白质相互作用。在苜蓿悬浮细胞培养中，诱导剂处理后 6 小时，前卫素还原酶和 DMI 脱水酶的活性增加了约 3 倍。活性在 40 小时内保持在最大水平，与细胞中 medicarpin 含量的稳定增加相关。发现通过前卫酮还原酶和 DMI 脱水酶的作用从前卫酮体外产生的药卡平是 (-)-药卡平（6aR，11aR-药卡平），与体内产生的药卡平具有相同的立体化学。
• Glycan therapeutics and related methods thereof
  申请人：KALEIDO BIOSCIENCES, INC.

  公开号：US10314853B2

  公开（公告）日：2019-06-11

  Preparations of glycan therapeutics, pharmaceutical compositions and medical foods thereof, optionally comprising micronutrients, polyphenols, prebiotics, probiotics, or other agents are provided and methods of making same. Also provided are methods of using said gycan therapeutics, e.g. for the modulation of human gastrointestinal microbiota and to treat dysbioses.

  本发明提供了可选择包含微量营养素、多酚、益生元、益生菌或其他制剂的聚糖疗法制剂、药物组合物及其医用食品，以及制造方法。还提供了使用所述糖治疗剂的方法，例如用于调节人类胃肠道微生物群和治疗菌群失调。