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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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
Publication status	Published - 30 Jul 2007

Keywords

Electrochemistry
Flavin model
Isotopic labeling

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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}",

year = "2007",

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day = "30",

doi = "10.1016/j.tetlet.2007.05.165",

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journal = "Tetrahedron Letters",

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TY - JOUR

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

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

UR - http://www.scopus.com/inward/record.url?scp=34347326072&partnerID=8YFLogxK

UR - http://ciencedirect.com/journal/tetrahedron-letters/vol/48/issue/31

U2 - 10.1016/j.tetlet.2007.05.165

DO - 10.1016/j.tetlet.2007.05.165

M3 - Article

AN - SCOPUS:34347326072

SN - 0040-4039

VL - 48

SP - 5517

EP - 5520

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

A flavin analogue with improved solubility in organic solvents

Abstract

Keywords

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