A flavin analogue with improved solubility in organic solvents

Ronald L. Koder, Bruce R. Lichtenstein, Jose F. Cerda, Anne Frances Miller, P. Leslie Dutton

Research output: Contribution to journalArticlepeer-review

11 Scopus citations


We report the synthesis and initial electrochemical characterization of a benzene-soluble flavin analogue: N(10)-2,2-dibenzylethyl-7,8-dimethylisoalloxazine (DBF, 1). This analogue, which has an unmodified flavin headgroup, is intended for use in the spectroscopic examination of the electronic effects of flavin hydrogen bonding in simple model systems in aprotic, non-hydrogen bonding solvents. With future spectroscopic studies in mind, we have developed a synthetic route, which allows the incorporation of isotopic labels using inexpensive starting materials.

Original languageEnglish
Pages (from-to)5517-5520
Number of pages4
JournalTetrahedron Letters
Issue number31
StatePublished - Jul 30 2007

Bibliographical note

Funding Information:
The authors would like to thank Dr. Colin Wraight of the Department of Biochemistry, the University of Illinois at Urbana-Champaigne for the kind donation of a sample of 2,2-dibenzylacetic acid to be used as a synthetic standard. This work was supported by DOE Grant DE-FG02-05ER46223 (P.L.D.), NIH grants GM41048 (P.L.D.), GM063921 (A.F.M.), NSF-MRSEC Grant DMR05-20020 (P.L.D.) and the Petroleum Research Fund via PRF #44321-AC4 (A.F.M.). R.L.K. was an NIH Postdoctoral Fellow (GM64090).


  • Electrochemistry
  • Flavin model
  • Isotopic labeling

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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