A flavin analogue with improved solubility in organic solvents

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

doi:10.1016/j.tetlet.2007.05.165

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 journal › Article › peer-review

11 Scopus citations

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.

Original language	English
Pages (from-to)	5517-5520
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	31
DOIs	https://doi.org/10.1016/j.tetlet.2007.05.165
State	Published - 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).

Keywords

Electrochemistry
Flavin model
Isotopic labeling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.05.165

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title = "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.",

keywords = "Electrochemistry, Flavin model, Isotopic labeling",

author = "Koder, {Ronald L.} and Lichtenstein, {Bruce R.} and Cerda, {Jose F.} and Miller, {Anne Frances} and Dutton, {P. Leslie}",

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). ",

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T1 - A flavin analogue with improved solubility in organic solvents

AU - Koder, Ronald L.

AU - Lichtenstein, Bruce R.

AU - Cerda, Jose F.

AU - Miller, Anne Frances

AU - Dutton, P. Leslie

N1 - 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).

PY - 2007/7/30

Y1 - 2007/7/30

N2 - 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.

AB - 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.

KW - Electrochemistry

KW - Flavin model

KW - Isotopic labeling

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SP - 5517

EP - 5520

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

A flavin analogue with improved solubility in organic solvents

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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