Abstract
Safranines hold great promise as artificial flavin-like electron transfer cofactors with tunable properties. We report the design and chemical synthesis of the p-methoxy derivative of safranine O using a new synthetic route based on the Ulmann condensation. Spectroelectrochemical comparison of the purified parent safranine and this derivative demonstrates that the modification increases its two-electron reduction potential by 125 mV, or 5.75 kcal/mol. This modification also causes redshifts in the absorbance and fluorescence spectra of the cofactor, suggesting that it may find future utility in arrayed sensor applications.
Original language | English |
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Pages (from-to) | 1201-1203 |
Number of pages | 3 |
Journal | Tetrahedron Letters |
Volume | 53 |
Issue number | 10 |
Early online date | 14 Dec 2011 |
DOIs | |
Publication status | Published - 7 Mar 2012 |
Keywords
- Enzyme design
- Reduction potential
- Safranine
- Ulmann condensation