Ec. Breinlinger et al., MODULATION OF FLAVIN RECOGNITION AND REDOX PROPERTIES THROUGH DONOR ATOM-PI INTERACTIONS, Journal of the American Chemical Society, 120(34), 1998, pp. 8606-8609
Computational and experimental model studies establish the importance
of donor atom-pi bonding on the recognition and function of flavins. T
his noncovalent interaction arises from electrostatic attraction betwe
en electron-rich (donor) atoms and electron-deficient aromatic systems
. The electrostatic origin of this bonding was verified through compar
ison of binding of model receptors to flavin in both oxidized (Fl(ox))
and radical anion (Fl(rad)(-)) forms: Interaction was strongest with
the electron-poor Fl(ox) and was greatly attenuated with the comparati
vely electron-rich Fl(rad)(-). Other factors determining the magnitude
s of these donor-pi interaction are the size and polarizability of the
donor atom.