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A Flavin Analogue with Improved Solubility in Organic Solvents.

ABSTRACT: 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.

SUBMITTER: Koder RL 

PROVIDER: S-EPMC2702786 | biostudies-literature | 2007 Jul

REPOSITORIES: biostudies-literature

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A Flavin Analogue with Improved Solubility in Organic Solvents.

Koder Ronald L RL   Lichtenstein Bruce R BR   Cerda Jose F JF   Miller Anne-Frances AF   Dutton P Leslie PL  

Tetrahedron letters 20070701 31

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 incorpo  ...[more]

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