Fluorine-19 NMR studies on the mechanism of riboflavin synthase. Synthesis of 6-(trifluoromethyl)-7-oxo-8-(D-ribityl)lumazine and 6-(trifluoromethyl)-7-methyl-8-(D-ribityl)lumazine
| Autor: | Hemantkumar H. Patel, Johannes Scheuring, Adelbert Bacher, Mark Cushman |
|---|---|
| Rok vydání: | 1992 |
| Předmět: |
chemistry.chemical_classification
Trifluoromethyl biology Bicyclic molecule Hydrochloride Stereochemistry Organic Chemistry Bacillus subtilis Nuclear magnetic resonance spectroscopy Fluorine-19 NMR biology.organism_classification chemistry.chemical_compound Riboflavin synthase Enzyme chemistry biology.protein |
| Zdroj: | The Journal of Organic Chemistry. 57:5630-5643 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo00047a015 |
| Popis: | The reactions of hexafluoropropene oxide (19), methyl trifluoropyruvate (21), and 1,1,1-trifluorobutane-2,3-dione (45) with a series of ortho diamines were investigated as an approach to the synthesis of trifluoromethyl-substituted quinoxalinones and lumazines. 6-(Trifluoromethyl)-7-oxo-8-(D-ribityl)lumazine (11) was synthesized by reaction of methyl trifluoropyruvate (21) with 5-amino-6-(D-ribitylamino)-2,4(1H,3H)-pyrimidinedione (3) hydrochloride and utilized as a 19 F NMR probe of the light riboflavin synthase of Bacillus subtilis |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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