Coenzyme models. 47. Synthesis and reactivity studies of novel flavinophanes and 5-deazaflavinophanes: correlation between flavin reactivity and ring strain

S Shinkai, A Kawase, T Yamaguchi…

Index: Shinkai, Seiji; Kawase, Akito; Yamaguchi, Toshiro; Manabe, Osamu; Wada, Yoshikazu; et al. Journal of the American Chemical Society, 1989 , vol. 111, # 13 p. 4928 - 4935

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Citation Number: 20

Abstract

Abstract: New flavinophanes Fl (n) and 5-deazaflavinophanes dFl (n) were synthesized in which N (3) and O (2') in the 10-(2-hydroxyphenyl) group were linked by a-(CH&-chain (n= 6, 7, 8, 10, and 12). In the'H NMR spectra the chemical shift of 9-H in the isoalloxazine ring and 6'-H in the 10-phenyl ring moved to lower magnetic field with decreasing ring size. The change corresponds to the decrease in the dihedral angle between the isoalloxazine ring ...