2001
DOI: 10.1089/15230860152665055
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Artificial Flavin Receptors: Effects of Hydrogen Bonding on Redox Properties of a Flavin Mimic

Abstract: This review describes the roles of hydrogen bonding on the redox properties of a flavin mimic by using artificial flavin receptors. The receptors exploited are melamine derivatives bearing guanidinium ion(s) that strongly bind 6-azaflavin through five or seven hydrogen bonds involving N(1), C(2)=O, N(3)-H, C(4)=O, N(5), and N(6) positions in CHCl3 and CHCl3-acetonitrile. It has been shown that receptors are quite useful for examination of the hydrogen bonding effects on the redox potential, stability of the an… Show more

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Cited by 8 publications
(2 citation statements)
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“…A molecule of FMN cofactor is bound noncovalently in the interior of the EcNR domain by a network of hydrogen bonds and van der Waals and electrostatic interactions. Flavin cofactor–protein interactions play a major role in the “tuning” of the redox potentials and activities of flavoproteins through the differential stabilization of each redox state 54–57. A positively charged amino acid positioned near the flavin ring stabilizes the anionic reduced states of the cofactor through favorable electrostatic interactions.…”
Section: Resultsmentioning
confidence: 99%
“…A molecule of FMN cofactor is bound noncovalently in the interior of the EcNR domain by a network of hydrogen bonds and van der Waals and electrostatic interactions. Flavin cofactor–protein interactions play a major role in the “tuning” of the redox potentials and activities of flavoproteins through the differential stabilization of each redox state 54–57. A positively charged amino acid positioned near the flavin ring stabilizes the anionic reduced states of the cofactor through favorable electrostatic interactions.…”
Section: Resultsmentioning
confidence: 99%
“…Furthermore, residues accepting/donating H-bonds found in close proximity to the flavin may also be involved in direct interactions with the isoalloxazine ring. This would cause a shift of redox potential in the positive direction by lowering flavin’s lowest unoccupied molecular orbital energy levels, as indicated previously. , …”
Section: Resultsmentioning
confidence: 59%