Model Systems for Flavoenzyme Activity: Relationships between Cofactor Structure, Binding and Redox Properties
A series of flavins were synthesized bearing electron-withdrawing and -donating substituents. The electrochemical properties of these flavins in a nonpolar solvent were determined. The recognition of these flavins by a diamidopyridine (DAP) receptor and the effect this receptor has on flavin redox potential was also quantified. It was found that the DAP-flavin binding affinity and the reduction potentials (E1/2) for both the DAP-bound and unbound flavins correlated well with functions derived from linear free energy relationships (LFERs). These results provide insight and predictive capability for the interplay of electronics and redox state-specific interactions for both abiotic and enzymatic systems.
Legrand, Yves-Marie,Gray, Mark,Cooke, Graeme,Rotello, Vincent M.
p. 15789 - 15795
(2007/10/03)
Efficient solution phase synthesis of 2-(N-acyl)-aminobenzimidazoles
An efficient solution phase protocol for the synthesis of 2-(N-acyl)-aminobenzimidazoles is reported. The 2-(N-acyl)-aminobenzimidazole ring system was assembled using SNAr reactions, nitro group reduction, acylthiourea formation and cyclization with EDC. The acyl protected 2-aminobenzimidazole derivatives were obtained in high yield and purity without purification of intermediates or final products. This reaction sequence eliminates the use of highly toxic cyanogen bromide, a reagent commonly used to prepare the 2-aminobenzimidazole ring system.
Seth, Punit P.,Robinson, Dale E.,Jefferson, Elizabeth A.,Swayze, Eric E.
p. 7303 - 7306
(2007/10/03)
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