Investigation of the Binding of Epimer A of the Covalent Hydrate of 6,7-Bis(trifluoromethyl)-8-d-ribityllumazine to a Recombinant F22W Bacillus subtilis Lumazine Synthase Mutant by 15N{19F} REDOR NMR

The two epimeric covalent hydrates A and B of 6,7-bis(trifluoromethyl)-8-d-ribityllumazine are metabolically stable analogues of hypothetical intermediates proposed in the reactions catalyzed by riboflavin synthase and lumazine synthase. To confirm the stereochemical assignments previously based sol...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-04, Vol.67 (7), p.2087-2092
Main Authors: Mehta, Anil K, Studelska, Daniel R, Fischer, Markus, Giessauf, Andreas, Kemter, Kristina, Bacher, Adelbert, Cushman, Mark, Schaefer, Jacob
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Summary:The two epimeric covalent hydrates A and B of 6,7-bis(trifluoromethyl)-8-d-ribityllumazine are metabolically stable analogues of hypothetical intermediates proposed in the reactions catalyzed by riboflavin synthase and lumazine synthase. To confirm the stereochemical assignments previously based solely on results for epimer B, a 15N{19F} REDOR NMR study was performed on the complex formed from epimer A and a recombinant, uniformly 15N-labeled F22W mutant of Bacillus subtilis lumazine synthase. The results indicate that the fluorines of the ligands are closer to the side chain nitrogens of Arg127 and farther away from the side chain nitrogens of Lys135 in epimer B than in epimer A. These results are consistent with the assignment of the earlier 7R configuration of epimer A and the 7S configuration of epimer B.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010920f