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Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles
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SYSNO ASEP 0368922 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis and structural studies of flavin and alloxazine adducts with O-nucleophiles Author(s) Ménová, P. (CZ)
Eigner, V. (CZ)
Čejka, J. (CZ)
Dvořáková, H. (CZ)
Šanda, Miloslav (UOCHB-X)
Cibulka, R. (CZ)Number of authors 6 Source Title Journal of Molecular Structure. - : Elsevier - ISSN 0022-2860
Roč. 1004, 1/3 (2011), s. 178-187Number of pages 10 s. Language eng - English Country NL - Netherlands Keywords alloxazine adducts ; flavin adducts ; flavoenzymes ; X-ray structural analysis ; NMR spectroscopy ; UV-VIS spectroscopy Subject RIV CC - Organic Chemistry R&D Projects GA203/07/1246 GA ČR - Czech Science Foundation (CSF) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000296927300024 DOI 10.1016/j.molstruc.2011.08.002 Annotation Five flavin (isoalloxazine) and alloxazine adducts with O-nucleophiles, 5-ethyl-4a-hydroxy-3,7,8,10-tetramethyl-4a,5-dihydroisoalloxazine (1a-OH), 5-ethyl-4a-hydroxy-3,10-dimethyl-4a,5-dihydroisoalloxazine (1b-OH), 5-ethyl-4a-methoxy-3,10-dimethyl-4a,5-dihydroisoalloxazine (1b-OMe), 5-ethyl-4a-hydroxy-1,3-dimethyl-4a,5-dihydroalloxazine (2a-OH) and 5-ethyl-4a-methoxy-1,3-dimethyl-4a,5-dihydroalloxazine (2a-OMe) were prepared from the corresponding salts, 5-ethyl-3,7,8,10-tetramethylisoalloxazinium (1a), 5-ethyl-3,10-dimethylisoalloxazinium (1b) and 5-ethyl-1,3-dimethylalloxazinium (2a) perchlorates by the addition of a nucleophile (water or methanol) and triethylamine as a base. They were characterized by 1H and 13C NMR, HR-MS and UV–VIS spectra and X-ray diffraction. Flavinium and alloxazinium salts are in rapid equilibria with their adducts; the equilibrium constants for flavin adduct formation is higher by six orders of magnitude than those for alloxazine derivatives. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2012
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