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Rhee, Hyun-Woo
Biomimetic Chemistry Lab
Research Interests
  • Site-Specific Protein Labeling in Living Cells
  • Artificial Cofactors for Biomimetic Catalyst
  • Spatiotemporal Proteome mapping of living cells

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A Bifunctional Molecule as an Artificial Flavin Mononucleotide Cyclase and a Chemosensor for Selective Fluorescent Detection of Flavins

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Title
A Bifunctional Molecule as an Artificial Flavin Mononucleotide Cyclase and a Chemosensor for Selective Fluorescent Detection of Flavins
Other Titles
A bifunctional molecule as an artificial flavin mononucleotide cyclase and a chemosensor for selective fluorescent detection of flavins
Author
Rhee, Hyun-WooChoi, So JungYoo, Sang HoJang, Yong OhPark, Hun HeeMaria Pinto, RosaCarlos Cameselle, JoseSandova, Francisco J.Roje, SanjaHan, KyungjaChung, Doo SooSuh, JunghunHong, Jong-In
Keywords
ADENINE-DINUCLEOTIDE; COPPER(II) COMPLEX; METAL-COMPLEXES; RIBOFLAVIN; HYDROLYSIS; FAD; CHEMISTRY
Issue Date
2009-07
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.131, no.29, pp.10107 - 10112
Abstract
Flavins, comprising flavin mononucleotide (FMN), flavin adenine dinucleotide (FAD), and riboflavin (RF, vitamin B-2), play important roles in numerous redox reactions such as those taking place in the electron-transfer chains of mitochondria in all eukaryotes and of plastids in plants. A selective chemosensor for flavins would be useful not only in the investigation of metabolic processes but also in the diagnosis of diseases related to flavins; such a sensor is presently unavailable. Herein, we report the first bifunctional chemosensor (PTZ-DPA) for flavins. PTZ-DPA consists of bis(Zn2+-dipicolylamine) and phenothiazine. Bis(Zn2+-dipicolylamine) (referred to here as XyDPA) was found to be an excellent catalyst in the conversion of FAD into cyclic FMN (riboflavin 4',5'-cyclic phosphate, cFMN) under physiological conditions, even at pH 7.4 and 27 degrees C, with less than 1 mol % of substrate. Utilizing XyDPA's superior function as an artificial FMN cyclase and phenothiazine as an electron donor able to quench the fluorescence of an isoalloxazine ring, PTZ-DPA enabled selective fluorescent discrimination of flavins (FMN, FAD, and RF): FAD shows ON(+), FMN shows OFF(-), and RF shows NO(0) fluorescence changes upon the addition of PTZ-DPA. With this selective sensing property, PTZ-DPA is applicable to real-time fluorescent monitoring of riboflavin kinase (RF to FMN), alkaline phosphatase (FMN to RF), and FAD synthetase (FMN to FAD)
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DOI
10.1021/ja9018012
ISSN
0002-7863
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PHY_Journal Papers
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