Fluorine-19 NMR studies of the mechanism of riboflavin synthase. Synthesis of 6-(trifluoromethyl)-8-(D-ribityl)lumazine and derivatives

Autor:	Hemantkumar H. Patel, Johannes Scheuring, Adelbert Bacher, Mark Cushman
Rok vydání:	1993
Předmět:	Trifluoromethyl biology Hydrochloride Stereochemistry Organic Chemistry Fluorine-19 NMR chemistry.chemical_compound Riboflavin synthase chemistry Pyran biology.protein Side chain Reactivity (chemistry) Hydrate
Zdroj:	The Journal of Organic Chemistry. 58:4033-4042
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00067a041
Popis:	6-(Trifluoromethyl)-8-(D-ribityl)lumazine (17) was synthesized in order to study its reactivity at C-7 and its binding to riboflavin synthase of Bacillus subtilis. Compound 17 was prepared by reaction of 5-amino-4-[(D-ribityl)amino]-2,4-(1H,3H)-pyrimidinedione hydrochloride (3-HCl) with trifluoropyruvaldehyde hydrate (18). NMR studies revealed that under basic conditions, 17 forms only one major anionic species in which the oxygen of the 3'-hydroxyl group on the ribityl side chain binds covalently to C-7 of the lumazine, resulting in the formation of a pyran ring
Databáze:	OpenAIRE
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