[7,9a-13C2]riboflavin | 482587-50-8

• 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: [7,9a-13C2]riboflavin
• 英文别名: 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
• CAS: 482587-50-8
• 化学式: C₁₇H₂₀N₄O₆
• 分子量: 378.347
• InChiKey: AUNGANRZJHBGPY-FWEUALQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [7,9a-13C2]riboflavin 在 riboflavin kinase 、 magnesium chloride pyruvate kinase 、 磷烯醇丙酮酸 、 5’-三磷酸腺苷 作用下， 以 various solvent(s) 为溶剂， 反应 16.0h， 生成 [7,9a-¹³C2]riboflavin mononucleotide
  参考文献：
  名称：

  Photochemically Induced Dynamic Nuclear Polarization in a C450A Mutant of the LOV2 Domain of the Avena sativa Blue-Light Receptor Phototropin

  摘要：

  Phototropin is a blue-light receptor involved in the phototropic response of higher plants. The photoreceptor comprises a protein kinase domain and two structurally similar flavin-mononucleotide (FMN) binding domains designated LOV1 and LOV2. Blue-light irradiation of recombinant LOV2 domains induces the formation of a covalent adduct of the thiol group of a functional cysteine in the cofactor-binding pocket to C(4a) of the FMN. Cysteine-to-alanine mutants of LOV domains are unable to form that adduct but generate an FMN radical upon illumination. The recombinant C450A mutant of the LOV2 domain of Avena sativa phototropin was reconstituted with universally and site-selectively C-13-labeled FMN and the C-13 NMR signals were unequivocally assigned. C-13 NMR spectra were acquired in darkness and under blue-light irradiation. The chemical shifts and the coupling patterns of the signals were not affected by irradiation. However, under blue-light exposure, exceptionally strong nuclear-spin polarization was developed in the resonances belonging to certain carbons of the FMN's isoalloxazine moiety. An enhancement of the NMR absorption was observed for the signals of C(5a), C(7), and C(9). NMR lines in emission were detected for the signals belonging to C(2), C(4), C(4a), C(6), C(8), and C(9a). The signal of C(10a) remained in absorption but was slightly attenuated. In contrast, the intensities of the NMR signals belonging to the carbons of the ribityl side chain of FMN were not affected by light. The observation of spin-polarized C-13-nuclei in the NMR spectra of the mutant LOV2 domain is clear evidence for radical-pair intermediates in the reaction steps following optical sample excitation.

  DOI：

  10.1021/ja053785n
• 作为产物：
  描述：

  5-nitroso-6-(D-ribitylamino)uracil 在 palladium on activated charcoal 氢气 、 5’-三磷酸腺苷 、 hexokinase 作用下， 以 various solvent(s) 为溶剂， 反应 72.0h， 生成 [7,9a-13C2]riboflavin
  参考文献：
  名称：

  Rapid One-Pot Synthesis of Riboflavin Isotopomers

  摘要：

  Flavocoenzymes labeled with stable isotopes are important reagents for the study of flavoproteins using isotope-sensitive methods such as NMR, ENDOR, infrared, and Raman spectroscopy. We describe highly versatile one-pot methods for the preparation of riboflavin isotopomers labeled with C-13 in every desired position of the xylene moiety. The starting materials are commercially available C-13-labeled glucose samples, which are converted into riboflavin using enzymes of the oxidative pentose phosphate pathway in combination with recombinant enzymes of the riboflavin biosynthetic pathway. The overall reaction comprises six enzyme-catalyzed reaction steps for the synthesis of the vitamin and two auxiliary enzymes for in situ recycling of cofactors. The overall yields of riboflavin based on isotope-labeled glucose are 35-50%.

  DOI：

  10.1021/jo026105x

文献信息

• Photochemically Induced Dynamic Nuclear Polarization in a C450A Mutant of the LOV2 Domain of the <i>Avena </i><i>s</i><i>ativa</i> Blue-Light Receptor Phototropin
  作者：Gerald Richter、Stefan Weber、Werner Römisch、Adelbert Bacher、Markus Fischer、Wolfgang Eisenreich

  DOI：10.1021/ja053785n

  日期：2005.12.1

  Phototropin is a blue-light receptor involved in the phototropic response of higher plants. The photoreceptor comprises a protein kinase domain and two structurally similar flavin-mononucleotide (FMN) binding domains designated LOV1 and LOV2. Blue-light irradiation of recombinant LOV2 domains induces the formation of a covalent adduct of the thiol group of a functional cysteine in the cofactor-binding pocket to C(4a) of the FMN. Cysteine-to-alanine mutants of LOV domains are unable to form that adduct but generate an FMN radical upon illumination. The recombinant C450A mutant of the LOV2 domain of Avena sativa phototropin was reconstituted with universally and site-selectively C-13-labeled FMN and the C-13 NMR signals were unequivocally assigned. C-13 NMR spectra were acquired in darkness and under blue-light irradiation. The chemical shifts and the coupling patterns of the signals were not affected by irradiation. However, under blue-light exposure, exceptionally strong nuclear-spin polarization was developed in the resonances belonging to certain carbons of the FMN's isoalloxazine moiety. An enhancement of the NMR absorption was observed for the signals of C(5a), C(7), and C(9). NMR lines in emission were detected for the signals belonging to C(2), C(4), C(4a), C(6), C(8), and C(9a). The signal of C(10a) remained in absorption but was slightly attenuated. In contrast, the intensities of the NMR signals belonging to the carbons of the ribityl side chain of FMN were not affected by light. The observation of spin-polarized C-13-nuclei in the NMR spectra of the mutant LOV2 domain is clear evidence for radical-pair intermediates in the reaction steps following optical sample excitation.
• Rapid One-Pot Synthesis of Riboflavin Isotopomers
  作者：Werner Römisch、Wolfgang Eisenreich、Gerald Richter、Adelbert Bacher

  DOI：10.1021/jo026105x

  日期：2002.12.1

  Flavocoenzymes labeled with stable isotopes are important reagents for the study of flavoproteins using isotope-sensitive methods such as NMR, ENDOR, infrared, and Raman spectroscopy. We describe highly versatile one-pot methods for the preparation of riboflavin isotopomers labeled with C-13 in every desired position of the xylene moiety. The starting materials are commercially available C-13-labeled glucose samples, which are converted into riboflavin using enzymes of the oxidative pentose phosphate pathway in combination with recombinant enzymes of the riboflavin biosynthetic pathway. The overall reaction comprises six enzyme-catalyzed reaction steps for the synthesis of the vitamin and two auxiliary enzymes for in situ recycling of cofactors. The overall yields of riboflavin based on isotope-labeled glucose are 35-50%.