8-Demethyl-8-(methylamino)riboflavin | 62746-55-8

• 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
• 英文名称: 8-Demethyl-8-(methylamino)riboflavin
• 英文别名: 8-methylamino-8-demethyl-riboflavin；7-methyl-8-methylamino-10-D-ribitol-1-yl-10H-benzo[g]pteridine-2,4-dione；7-methyl-8-(methylamino)-10-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione；8-Methylamino-riboflavin；7-methyl-8-(methylamino)-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
• CAS: 62746-55-8
• 化学式: C₁₇H₂₁N₅O₆
• 分子量: 391.384
• InChiKey: PWZSYWZSTDXLFL-SCRDCRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  167
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  玫瑰黄色素 在 水 作用下， 反应 2.0h， 生成 8-Demethyl-8-(methylamino)riboflavin 、 8-Amino-8-norriboflavin
  参考文献：
  名称：

  Photo-degradation behaviour of roseoflavin in some aqueous solutions

  摘要：

  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.

  DOI：

  10.1016/j.chemphys.2010.02.004

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。
• 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。
• [EN] METHODS FOR INHIBITING BACTERIA GROWTH<br/>[FR] PROCÉDÉS D'INHIBITION DE LA CROISSANCE BACTÉRIENNE
  申请人：BIORELIX INC

  公开号：WO2013040412A2

  公开（公告）日：2013-03-21

  The present invention is directed to compositions and methods of inhibiting the growth of a bacteria comprising contacting or exposing a bacteria to a compound which binds to a riboswitch to induce expression of at least one gene.
• Structural and kinetic studies on RosA, the enzyme catalysing the methylation of 8-demethyl-8-amino-<scp>d</scp> -riboflavin to the antibiotic roseoflavin
  作者：Chanakan Tongsook、Michael K. Uhl、Frank Jankowitsch、Matthias Mack、Karl Gruber、Peter Macheroux

  DOI：10.1111/febs.13690

  日期：2016.4

  N,N-8-demethyl-8-amino-D-riboflavin dimethyltransferase (RosA) catalyzes the final dimethylation of 8-demethyl-8-amino-D-riboflavin (AF) to the antibiotic roseoflavin (RoF) in Streptomyces davawensis. In the present study we have solved the X-ray structure of RosA and determined the binding properties of substrates and products. Moreover, we have used steady-state and rapid reaction kinetics to obtain

  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-
• 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.