Coenzyme models

Lightening flavin by amination for fluorescent sensing

“…44 Recently, enhanced UV-vis absorption was reported for some AmFLs, such as 8-aminoriboflavin, 8-amino-7-methyl-flavin and 8-amino-7-methyl-5-ethylflavinum, etc., and strong green fluorescence were also reported in nonpolar solution of these AmFLs. 41,47,48,[58][59][60][61] The mechanisms for such enhancements, as well as the structure-dependent photophysical properties of AmFLs that may benefit the design of functionalized FL, call for additional theoretical efforts. 23,47,62,63 Inspired by the pioneering works on the design of ROS sensors and the promising performance of FL-based fluorescent sensors, [35][36][37][38][39] we performed extensive DFT-and TD-DFT-based calculations, as well as simulations within the Thermal Vibration Correlation Function (TVCF) formalism [64][65][66][67][68][69] to predict the photophysical properties of AmFLs (Fig.…”

“…, and strong green fluorescence were also reported in nonpolar solution of these AmFLs. 41,47,48,58–61 The mechanisms for such enhancements, as well as the structure-dependent photophysical properties of AmFLs that may benefit the design of functionalized FL, call for additional theoretical efforts. 23,47,62,63…”

Model systems for flavoenzyme activity: an electrochemically tuneable model of roseoflavinElectronic supplementary information (ESI) available: synthesis of 2, CV and spectral data. See http://www.rsc.org/suppdata/cc/b4/b401470g/

“…For example, roseoflavin models have been prepared in order to investigate the role solvent polarity has in modulating the reactivity of these systems. 5 Although these investigations have indicated that roseoflavin may become activated when bound to the hydrophobic pocket of an enzyme, the role more specific interactions (e.g. hydrogen bonding) have in controlling the redox properties of this unit has not been reported.…”