Functionalized flavin receptors. Regulation of redox properties of 6-azaflavin via hydrogen bondings with melamine derivatives bearing guanidinium ion (s) in organic …

…, T Kuroi, S Kondo, T Nabeshima, Y Yano

Index: Kajiki, Takeshi; Moriya, Hideki; Hoshino, Kazuhiko; Kuroi, Tadashi; Kondo, Shin-Ichi; Nabeshima, Tatsuya; Yano, Yumihiko Journal of Organic Chemistry, 1999 , vol. 64, # 26 p. 9679 - 9689

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Citation Number: 29

Abstract

Melamine derivatives bearing guanidinium ion (s) were synthesized as a flavin receptor using hydrogen bonds. The receptors bind 6-aza-10-dodecylisoalloxazine (6-azaflavin, 6- AzaFl) quite strongly via five or seven hydrogen bonds in CHCl3 or CHCl3-MeCN. Redox potentials of 6-AzaFl were considerably affected by hydrogen bondings of the receptors (positive shift: Δ E 1/2= 220-317 mV). Anionic semiquinone radical of 6-AzaFl was found to ...