8-Amino-8-norriboflavin | 5178-05-2

• 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-Amino-8-norriboflavin
• 英文别名: 8-Amino-8-demethylriboflavin；8-amino-7-methyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
• CAS: 5178-05-2
• 化学式: C₁₆H₁₉N₅O₆
• 分子量: 377.357
• InChiKey: BZHBNLOEUZEUOA-LOWVWBTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  181
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-Amino-8-norriboflavin 在 sodium dithionite 、 recombinant human flavokinase 、 sodium fluoride 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 反应 0.25h， 生成 8-demethyl-8-amino-riboflavin 5'-phosphate
  参考文献：
  名称：

  The antibiotics roseoflavin and 8-demethyl-8-amino-riboflavin from Streptomyces davawensis are metabolized by human flavokinase and human FAD synthetase

  摘要：

  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.

  DOI：

  10.1016/j.bcp.2011.08.029
• 作为产物：
  描述：

  D-核糖 在 palladium 10% on activated carbon 、 氨 、 氢气 、 硼酸 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 20.0~105.0 ℃ 、100.0 kPa 条件下， 反应 66.0h， 生成 8-Amino-8-norriboflavin
  参考文献：
  名称：

  在玫瑰黄素生物合成过程中，用氨基取代核黄素 C8 甲基的显着氧化级联

  摘要：

  玫瑰黄素是一种天然存在的核黄素类似物，具有抗生素特性。它是由核黄素在涉及用二甲氨基取代 C8 甲基的反应中生物合成的。在此，我们报告了一种黄素依赖性酶的鉴定，该酶通过 8-甲酰基-FMN 的中介作用将黄素单核苷酸 (FMN) 和谷氨酸转化为 8-氨基-FMN。提出了针对这一显着转变的机械建议。

  DOI：

  10.1021/jacs.6b02469

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。
• An Improved Synthesis of 8-Amino-8-demethylriboflavin
  作者：Sabu Kasai、Bernhard J. Fritz、Kunio Matsui

  DOI：10.1246/bcsj.60.3041

  日期：1987.8

  8-Amino-8-demethylriboflavin was synthesized from 3-nitro-4-methylaniline N-d-riboside by selective reduction of the N-glycoside with sodium borohydride, followed by hydrogenation of the nitro group in the presence of Raney’s catalyst. The obtained phenylenediamine was condensed with violuric acid to give the flavin in a high yield.

  8-氨基-8-去甲基核黄素是通过选择性还原3-硝基-4-甲基苯胺N-d-核糖苷，使用氢化钠还原N-糖苷，随后在Raney催化剂的存在下对硝基进行氢化反应合成的。获得的苯二胺与维奥鲁酸缩合，得到高产率的黄素。
• 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-
• 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。
• 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.