dihydrobisnoryangonin | 920318-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: dihydrobisnoryangonin
• 英文别名: dihydro-BNY；4-Hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-2H-pyran-2-one；4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]pyran-2-one
• CAS: 920318-17-8
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: KKLHRBKHXBCHPR-UHFFFAOYSA-N

物化性质

• 沸点：
  453.2±45.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-hydroxyphenylpropionyl-CoA 、 丙二酰辅酶A-钠盐 在 Oryza sativa curcuminoid synthase 作用下， 反应 3.0h， 以35%的产率得到dihydrobisnoryangonin
  参考文献：
  名称：

  通过来自稻的类姜黄素合酶一锅形成二芳基庚烷支架的结构基础。

  摘要：

  来自水稻的类姜黄素合酶 (CUS) 是一种植物特异性 III 型聚酮化合物合酶 (PKS)，可催化双去甲氧基姜黄素的 C(6)-C(7)-C(6) 二芳基庚烷类支架的显着单锅形成，通过两分子 4-香豆酰辅酶 A 和一分子丙二酰辅酶 A 的缩合。O. sativa CUS 的晶体结构以 2.5-A 的分辨率解析，揭示了一种独特的向下扩展的活性位点结构，以前在已知的 III 型 PKS 中未发现。大的活性位点腔足够长以容纳两个 C(6)-C(3) 香豆酰单元和一个丙二酰单元。此外，晶体结构表明存在推定的亲核水分子，该分子与 Ser351-Asn142-H(2)O-Tyr207-Glu202 形成氢键网络，邻近活性中心的催化 Cys174。这些观察结果表明，CUS 采用独特的催化机制，用于 C(6)-C(7)-C(6) 支架的一锅形成。因此，CUS 利用亲核水在双酮阶段终止初始聚酮链延长。酶结合中间体的硫酯键断裂产生

  DOI：

  10.1073/pnas.1011499107

文献信息

• Reshaping the 2‐Pyrone Synthase Active Site for Chemoselective Biosynthesis of Polyketides
  作者：Yu Zhou、Evan N. Mirts、Sangdo Yook、Matthew Waugh、Rachel Martini、Yong‐Su Jin、Yi Lu

  DOI：10.1002/anie.202212440

  日期：2023.1.26

  Implementation of novel synthetic pathways into metabolic network is challenging. Empowered by protein engineering and synthetic biology, a whole-cell transformation process is reported to utilize engineered 2-pyrone synthase with novel reactivity in metabolic networks to convert carboxylic acids and intracellular malonyl-CoA directly into the pyrone products with high yields, catalytic efficiency and good selectivity

  将新的合成途径实施到代谢网络中具有挑战性。据报道，在蛋白质工程和合成生物学的支持下，全细胞转化过程利用在代谢网络中具有新颖反应性的工程化 2-吡喃酮合酶，将羧酸和细胞内丙二酰辅酶 A 直接转化为吡喃酮产品，具有高产率、催化效率和良好的选择性。
• Synthesis of non-natural flavanones and dihydrochalcones in metabolically engineered yeast
  作者：Sean R. Werner、Hao Chen、Hanxiao Jiang、John A. Morgan

  DOI：10.1016/j.molcatb.2010.05.017

  日期：2010.10

  Flavonoids are plant phenolic compounds that have many interesting medicinal properties. Therefore, there is interest in the synthesis of non-natural flavonoids as they may possess new or enhanced biological activities. In this study, metabolically engineered Saccharomyces cerevisiae expressing 4-coumaroyl:CoA-ligase (4CL) and chalcone synthase (CHS) was explored as a platform for producing non-natural flavanones and dihydrochalcones. By precursor addition of cinnamic acid analogues to the engineered yeast, numerous non-natural flavanones and dihydrochalcones were formed in vivo. Also, several CHS derailment products were formed. Of the isolated compounds, one flavanone and three derailment products were found to be novel compounds. (C) 2010 Elsevier B.V. All rights reserved.
• ENZYMATIC SYNTHESIS OF KAVALACTONES AND FLAVOKAVAINS
  申请人：Whitehead Institute for Biomedical Research

  公开号：US20190271015A1

  公开（公告）日：2019-09-05

  Disclosed are methods, compositions, proteins, nucleic acids, cells, vectors, compounds, reagents, and systems for the preparation of kavalactones, flavokavains, and kavalactone and flavokavain biosynthetic intermediates using enzymes expressed in heterologous host cells, such as microorganisms or plants, or using in vitro enzymatic reactions. This invention also provides for the expression of the enzymes by recombinant cell lines and vectors. Furthermore, the enzymes can be components of constructs such as fusion proteins. The kavalactones produced can be utilized to treat anxiety disorder, insomnia, and other psychological and neurological disorders. The flavokavains produced can be utilized to treat various cancers including colon, bladder, and breast cancers.
• Structural basis for the one-pot formation of the diarylheptanoid scaffold by curcuminoid synthase from <i>Oryza sativa</i>
  作者：Hiroyuki Morita、Kiyofumi Wanibuchi、Hirohiko Nii、Ryohei Kato、Shigetoshi Sugio、Ikuro Abe

  DOI：10.1073/pnas.1011499107

  日期：2010.11.16

  Curcuminoid synthase (CUS) from Oryza sativa is a plant-specific type III polyketide synthase (PKS) that catalyzes the remarkable one-pot formation of the C(6)-C(7)-C(6) diarylheptanoid scaffold of bisdemethoxycurcumin, by the condensation of two molecules of 4-coumaroyl-CoA and one molecule of malonyl-CoA. The crystal structure of O. sativa CUS was solved at 2.5-A resolution, which revealed a unique

  来自水稻的类姜黄素合酶 (CUS) 是一种植物特异性 III 型聚酮化合物合酶 (PKS)，可催化双去甲氧基姜黄素的 C(6)-C(7)-C(6) 二芳基庚烷类支架的显着单锅形成，通过两分子 4-香豆酰辅酶 A 和一分子丙二酰辅酶 A 的缩合。O. sativa CUS 的晶体结构以 2.5-A 的分辨率解析，揭示了一种独特的向下扩展的活性位点结构，以前在已知的 III 型 PKS 中未发现。大的活性位点腔足够长以容纳两个 C(6)-C(3) 香豆酰单元和一个丙二酰单元。此外，晶体结构表明存在推定的亲核水分子，该分子与 Ser351-Asn142-H(2)O-Tyr207-Glu202 形成氢键网络，邻近活性中心的催化 Cys174。这些观察结果表明，CUS 采用独特的催化机制，用于 C(6)-C(7)-C(6) 支架的一锅形成。因此，CUS 利用亲核水在双酮阶段终止初始聚酮链延长。酶结合中间体的硫酯键断裂产生