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Literature DB >> 19568318

A Flavin Analogue with Improved Solubility in Organic Solvents.

Ronald L Koder¹, Bruce R Lichtenstein, Jose F Cerda, Anne-Frances Miller, P Leslie Dutton.

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.

Entities: Chemical

Year: 2007 PMID： 19568318 PMCID： PMC2702786 DOI： 10.1016/j.tetlet.2007.05.165

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

11 in total

1. Comparing protein-ligand interactions in solution and single crystals by Raman spectroscopy.

Authors: M D Altose; Y Zheng; J Dong; B A Palfey; P R Carey
Journal: Proc Natl Acad Sci U S A Date: 2001-03-06 Impact factor: 11.205

Review 2. Advances in flavin and flavoprotein optical spectroscopy.

Authors: R J Stanley
Journal: Antioxid Redox Signal Date: 2001-10 Impact factor: 8.401

3. Model systems for flavoenzyme activity. Control of flavin recognition via specific electrostatic interactions.

Authors: A J Goodman; E C Breinlinger; C M McIntosh; L N Grimaldi; V M Rotello
Journal: Org Lett Date: 2001-05-17 Impact factor: 6.005

4. 15N solid-state NMR provides a sensitive probe of oxidized flavin reactive sites.

Authors: Ronald L Koder; Joseph D Walsh; Maxim S Pometun; P Leslie Dutton; Richard J Wittebort; Anne-Frances Miller
Journal: J Am Chem Soc Date: 2006-11-29 Impact factor: 15.419

5. Syntheses of isoalloxazines and isoalloxazine 5-oxides. A new synthesis of riboflavin.

Authors: F Yoneda; Y Sakuma; M Ichiba; K Shinomura
Journal: J Am Chem Soc Date: 1976-02-04 Impact factor: 15.419

6. The reaction between o-aminoazo compounds and barbituric acid; a new synthesis of riboflavin.

Authors: M TISHLER; K PFISTER
Journal: J Am Chem Soc Date: 1947-06 Impact factor: 15.419

7. Flavin thermodynamics explain the oxygen insensitivity of enteric nitroreductases.

Authors: Ronald L Koder; Chad A Haynes; Michael E Rodgers; David W Rodgers; Anne-Frances Miller
Journal: Biochemistry Date: 2002-12-03 Impact factor: 3.162

8. Synthesis, Structure, and Nucleophile-Induced Rearrangements of Spiroketones.

Authors: Przemyslaw Maslak; Sridhar Varadarajan; Jeffrey D. Burkey
Journal: J Org Chem Date: 1999-10-29 Impact factor: 4.354

9. Further branching of valproate-related carboxylic acids reduces the teratogenic activity, but not the anticonvulsant effect.

Authors: U Bojic; M M Elmazar; R S Hauck; H Nau
Journal: Chem Res Toxicol Date: 1996 Jul-Aug Impact factor: 3.739