F. Bosca et al., Substituent effects on electrophilicity of flavins: an experimental and semi-empirical molecular orbital study, J PHOTOCH B, 55(2-3), 2000, pp. 183-187
Citations number
16
Categorie Soggetti
Biochemistry & Biophysics
Journal title
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY
The reactivities of the triplet excited states of several flavins with diff
erent N(10)-phenyl substituents have been found to be very similar. There i
s a good correlation between semi-empirical molecular orbital calculations
at the MINDO/AM1 level and observed redox potentials. However, the most int
eresting observation is that the substituent effects are very small; this s
uggests that the N(10)-phenyl substituents are nearly perpendicular to the
plane of the main ring due to their steric interactions with the main isoal
loxazine system. Computed calculations as well as the fact that similar abs
orption maxima are obtained for 3-methyl-10-phenylisoalloxazine and 3-methy
l-10-methylisoalloxazine are in agreement with this prediction. (C) 2000 El
sevier Science S.A. All rights reserved.