Coenzyme models. 30. On the unusual spectroscopic behaviors of amphiphilic flavins and 5-deazaflavins.
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概要
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At room temperature in aqueous solution, isoalloxazines and 5-deazaisoalloxazines with 10- dodecyl substituent gave a well-resolved, three-banded Sl peak which has been believed to appear only in nonpolar solvents or in enzymic hydrophobic pockets where isoalloxazines and 5-deazaisoalloxazines become free of hydrogen-bonding effects. On the other hand, 3-methyl-10-ethylisoalloxazine and 5-deazaisoalloxazines with 10- ethyl or 10- octyl group did not give such a fine-structured Sl peak. We have found that (i) the fine structure disappears on the addition of organic solvents (ethanol>40 vol% or pyridine>20 vol%), (ii) the fine structure also disappears on the addition of surfactants (CTAB, Brij-35, and SDS) above the critical micelle concentrations, (iii) 10-dodecylisoalloxazine with hydrophilic 3-(thiazolinio)propyl group at 3-position has not the fine structure, and (iv) the fluorescent intensity of 3-methyl-10-dodecyl-5-deazaisoalloxazine is much weaker than that of 3-methyl-10-ethyl-5-deazaisoalloxazine in aqueous solution but these intensities become comparable above 40 vol% ethanol. These findings are consistently rationalized in terms of an aggregation-deaggregation equilibrium of amphiphilic flavin analogues, supporting that the fine structure in aqueous solution is due to the "stacking" association of (5-deaza)isoalloxazine nuclei, like that of dye molecules. The aggregation-deaggregation phenomenon is sensitively reflected by the reactivity: the reaction of 3-methyl-10-ethyl-5-deazaisoalloxazine and cyanide ion gave <I>k</I><SUB>2</SUB>=1.27 M<SUP>−1</SUP> s<SUP>−1</SUP> in aqueous solution at 30 °C, whereas aggregated 3-methyl-10-dodecyl-5-deazaisoalloxazine did not react with cyanide ion. These findings have significant implications on the chemistry of flavoproteins, because the absorption spectra of enzyme-bound flavins and 5-deazaflavins have frequently been cited to discuss the flavin reactivities.
- 公益社団法人 日本化学会の論文
著者
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Shinkai Seiji
Department Of Applied Chemistry Faculty Of Engineering Kyushu University
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Yoneda Fumio
Faculty Of Pharmaceutical Sciences Kyoto University
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Harada Akiko
Department Of Biology Faculty Of Science Kyushu University
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MANABE Osamu
Department of Applied Chemistry, Faculty of Engineering, Nagasaki University
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Harada Akiko
Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University
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