玫瑰黄色素 | 51093-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 中文名称: 玫瑰黄色素
• 英文名称: roseoflavin
• 英文别名: 8-(dimethylamino)-7-methyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
• CAS: 51093-55-1
• 化学式: C₁₈H₂₃N₅O₆
• 分子量: 405.411
• InChiKey: IGQLDUYTWDABFK-GUTXKFCHSA-N

物化性质

• 熔点：
  276-278°C
• 密度：
  1.59±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  8

制备方法与用途

生物活性

Roseoflavin 是一种天然色素，最初从 Streptomyces davawensis 中分离出来。它是核黄素和黄素单核苷酸（FMN）的抗代谢类似物，并具有抗菌作用。

体外研究

Roseoflavin 能够直接与 FMN 核糖开关 aptamer 结合（解离常数 ( K_d ) 约为 100 nM），从而下调枯草芽孢杆菌（B. subtilis）中 FMN 核糖开关 - lacZ 报告基因 的表达。

反应信息

• 作为反应物：
  描述：

  玫瑰黄色素 在 sodium hydroxide 、 溶剂黄146 作用下， 以87%的产率得到6-(dimethylamino)-7-methyl-3-oxo-4-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]quinoxaline-2-carboxylic acid
  参考文献：
  名称：

  WO2020117974A5

  摘要：

  公开号：

  WO2020117974A5
• 作为产物：
  描述：

  8-Demethyl-8-(methylamino)riboflavin 、 S-(5’-腺苷基)-L-氯化蛋氨酸 在 N,N-8-demethyl-8-amino-D-riboflavin dimethyltransferase 、 sodium chloride 作用下， 以 aq. buffer 为溶剂， 生成 玫瑰黄色素
  参考文献：
  名称：

  RosA的结构和动力学研究，该酶催化8-demethyl-8-氨基-D-核黄素甲基化为抗生素玫瑰黄素。

  摘要：

  N，N-8-去甲基-8-氨基-D-核黄素二甲基转移酶（RosA）催化8脱甲基-8-氨基-D-核黄素（AF）在达维链霉菌中的最终的二甲基化成抗生素玫瑰黄素（RoF）。在本研究中，我们已经解决了RosA的X射线结构，并确定了底物和产品的结合特性。此外，我们使用稳态和快速反应动力学来获得有关反应机理的详细信息。发现RosA的结构类似于先前确定的S-腺苷甲硫氨酸（SAM）依赖性甲基转移酶，其特征在于两个结构域，主要是α-螺旋“正交束”和Rossmann-样结构域（α/β扭曲的开孔）。生物信息学和分子建模使我们能够预测RosA中潜在的SAM和AF结合位点，这表明两种底物，AF和SAM可以独立绑定到各自的绑定袋。动力学实验证实了这一点，该实验证明了随机顺序的bi-bi反应机理。此外，我们已经通过等温滴定量热法或UV-Vis吸收光谱法确定了底物和产物的解离常数。这表明与底物AF和SAM相比，RoF和S-

  DOI：

  10.1111/febs.13690

文献信息

• [EN] FLAVIN DERIVATIVES<br/>[FR] DÉRIVÉS DE LA FLAVINE
  申请人：BIORELIX PHARMACEUTICALS INC

  公开号：WO2010019208A1

  公开（公告）日：2010-02-18

  The present invention relates novel flavin derivatives and other flavin derivatives, their use and compositions for use as riboswitch ligands and/or anti-infectives. The invention also provides method of making novel flavin derivatives.

  本发明涉及新型黄素衍生物和其他黄素衍生物，它们的用途以及用作核糖开关配体和/或抗感染剂的组合物。该发明还提供了制备新型黄素衍生物的方法。
• Broadening the Scope of the Flavin‐Tag Method by Improving Flavin Incorporation and Incorporating Flavin Analogs
  作者：Yapei Tong、Marnix R. Loonstra、Marco W. Fraaije

  DOI：10.1002/cbic.202200144

  日期：2022.6.3

  Flavin-tag 2.0: The Flavin-tag method can be used for labelling of proteins with various chromo- and fluorophores and redox-active probes, including flavin (yellow), roseoflavin (red), 5-deazaflavin (fluorescent), and nicotinamide.

  Flavin-tag 2.0：Flavin-tag 方法可用于用各种发色团和荧光团以及氧化还原活性探针标记蛋白质，包括黄素（黄色）、玫瑰黄素（红色）、5-脱氮杂黄素（荧光）和烟酰胺。
• FLAVIN DERIVATIVES
  申请人：Gadwood Robert

  公开号：US20120077781A1

  公开（公告）日：2012-03-29

  The present invention relates novel flavin derivatives and other flavin derivatives, their use and compositions for use as riboswitch ligands and/or anti-infectives. The invention also provides method of making novel flavin derivatives.

  本发明涉及新型的黄素衍生物和其他黄素衍生物，它们的用途和组合物用作核糖开关配体和/或抗感染剂。本发明还提供了制备新型黄素衍生物的方法。
• The antibiotics roseoflavin and 8-demethyl-8-amino-riboflavin from Streptomyces davawensis are metabolized by human flavokinase and human FAD synthetase
  作者：Danielle B. Pedrolli、Shinobu Nakanishi、Maria Barile、Madina Mansurova、Eleonora C. Carmona、Andreas Lux、Wolfgang Gärtner、Matthias Mack

  DOI：10.1016/j.bcp.2011.08.029

  日期：2011.12

  The non-pathogenic Gram-positive soil bacterium Streptomyces davawensis synthesizes the riboflavin (vitamin B-2) analogs roseoflavin (RoF) and 8-demethyl-8-amino-riboflavin (AF). Both compounds are antibiotics. Notably, a number of other riboflavin analogs are currently under investigation with regard to the development of novel antiinfectives. As a first step towards understanding the metabolism of riboflavin analogs in humans, the key enzymes flavokinase (EC 2.7.1.26) and FAD synthetase (EC 2.7.7.2) were studied. Human flavokinase efficiently converted RoF and AF to roseoflavin mononucleotide (RoFMN) and 8-demethyl-8-amino-riboflavin mononucleotide (AFMN), respectively. Human FAD synthetase accepted RoFMN but not AFMN as a substrate. Consequently, roseoflavin adenine dinucleotide (RoFAD) was synthesized by the latter enzyme but not 8-demethyl-8-amino-riboflavin adenine dinucleotide (AFAD). The cofactor analogs RoFMN, AFMN and RoFAD have different physicochemical properties as compared to FMN and FAD. Thus, the cofactor analogs have the potential to render flavoenzymes inactive, which may negatively affect human metabolism. RoF, but not AF, was found to inhibit human flavokinase. In summary, we suggest that AF has a lower toxic potential and may be better suited as a lead structure to develop antimicrobial compounds. (C) 2011 Elsevier Inc. All rights reserved.
• Photo-degradation behaviour of roseoflavin in some aqueous solutions
  作者：A. Tyagi、A. Penzkofer、T. Mathes、P. Hegemann

  DOI：10.1016/j.chemphys.2010.02.004

  日期：2010.3

  An absorption and emission spectroscopic characterization of roseoflavin (8-dimethylamino-8-demethylriboflavin, RoF) in aqueous solutions was carried out. The studies were concentrated on roseoflavin in pH 8 phosphate buffer. Absorption cross-section spectra, fluorescence excitation spectra, fluorescence quantum distributions, fluorescence quantum yields and fluorescence lifetimes were determined. The fluorescence of RoF is quenched by photo-induced intra-molecular charge-transfer at room temperature. The photo-degradation of RoF in un-buffered water, in Tris-HCl buffer, and in phosphate buffer was studied. Phosphate buffer and to a smaller extent Tris buffer catalyse the RoF photo-degradation. Photo-excitation of the primary photoproduct, 8-methylamino-riboflavin (8-MNH-RF), enhanced the RoF degradation by triplet 8-MNH-RF - singlet RoF excitation transfer with subsequent triplet-state RoF degradation. (C) 2010 Elsevier B.V. All rights reserved.