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

Producción científica: Article › revisión exhaustiva

11 Citas (Scopus)

Resumen

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.

Idioma original	English
Páginas (desde-hasta)	5517-5520
Número de páginas	4
Publicación	Tetrahedron Letters
Volumen	48
N.º	31
DOI	https://doi.org/10.1016/j.tetlet.2007.05.165
Estado	Published - jul 30 2007

Nota bibliográfica

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).

Financiación

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).

Financiadores	Número del financiador
NSF MRSEC	DMR05-20020
National Institutes of Health (NIH)	GM41048, GM063921
Michigan State University-U.S. Department of Energy (MSU-DOE) Plant Research Laboratory	DE-FG02-05ER46223
American Chemical Society Petroleum Research Fund	44321-AC4

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Acceder al documento

10.1016/j.tetlet.2007.05.165

Otros archivos y enlaces

Citar esto

@article{d10eea7b1e5f4db7921abec287c3f5f8,

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). ",

year = "2007",

month = jul,

day = "30",

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

language = "English",

volume = "48",

pages = "5517--5520",

number = "31",

}

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

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

UR - https://www.scopus.com/pages/publications/34347326072

UR - https://www.scopus.com/pages/publications/34347326072#tab=citedBy

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

Resumen

Nota bibliográfica

Financiación

ASJC Scopus subject areas

Acceder al documento

Otros archivos y enlaces

Huella

Citar esto