Manipulating reduction potentials in an artificial safranin cofactor

Gheevarghese Raju, Joseph Capo, Bruce R. Lichtenstein, Jose F. Cerda, Ronald L. Koder*

*Corresponding author for this work

Research output: Contribution to journalLetterpeer-review


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 languageEnglish
Pages (from-to)1201-1203
Number of pages3
JournalTetrahedron Letters
Issue number10
Early online date14 Dec 2011
Publication statusPublished - 7 Mar 2012


  • Enzyme design
  • Reduction potential
  • Safranine
  • Ulmann condensation


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