917752-09-1

Basic information

• Product Name: N-⁽¹⁰⁾-2,2-dibenzylethyl-7,8-dimethylisoalloxazine
• Synonyms: N-⁽¹⁰⁾-2,2-dibenzylethyl-7,8-dimethylisoalloxazine
• CAS NO: 917752-09-1
• Molecular Weight: 450.54
• Mol File: 917752-09-1.mol

Chemical Properties

• CAS DataBase Reference: N-⁽¹⁰⁾-2,2-dibenzylethyl-7,8-dimethylisoalloxazine(CAS DataBase Reference)
• NIST Chemistry Reference: N-⁽¹⁰⁾-2,2-dibenzylethyl-7,8-dimethylisoalloxazine(917752-09-1)
• EPA Substance Registry System: N-⁽¹⁰⁾-2,2-dibenzylethyl-7,8-dimethylisoalloxazine(917752-09-1)

Safety Data

• Hazardous Substances Data: 917752-09-1(Hazardous Substances Data)

Upstream product

• 67-52-7 BARBITURIC ACID 
• 618-68-8 2-benzyl-3-phenylpropanoic acid 
• 597-55-7 dibenzylmalonic acid diethyl ester 
• 948828-91-9 1-(2,2-dibenzylethylamino)-3,4-dimethylbenzene 
• 948828-90-8 1-(2,2-dibenzylethylamido)-3,4-dimethylbenzene 

Relevant articles and documents

A flavin analogue with improved solubility in organic solvents

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.

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

Flavins are central to the reactivity of a wide variety of enzymes and electron transport proteins. There is great interest in understanding the basis for the different reactivities displayed by flavins in different protein contexts. We propose solid-state nuclear magnetic resonance (SS-NMR) as a tool for directly observing reactive positions of the flavin ring and thereby obtaining information on their frontier orbitals. We now report the SS-NMR signals of the redox-active nitrogens N1 and N5, as well as that of N3. The chemical shift tensor of N5 is over 720 ppm wide, in accordance with the predictions of theory and our calculations. The signal of N3 can be distinguished on the basis of coupling to 1H absent for N1 and N5, as well as the shift tensor span of only 170 ppm, consistent with N3's lower aromaticity and lack of a nonbonding lone pair. The isotropic shifts and spans of N5 and N1 reflect two opposite extremes of the chemical shift range for "pyridine-type" N's, consistent with their electrophilic and nucleophilic chemical reactivities, respectively. Upon flavin reduction, N5's chemical shift tensor contracts dramatically to a span of less than 110 ppm, and the isotropic chemical shift changes by approximately 300 ppm. Both are consistent with loss of N5's nonbonding lone pair and decreased aromaticity, and illustrate the responsiveness of the 15N chemical shift principal values to electronic structure. Thus. 15N chemical shift principal values promise to be valuable tools for understanding electronic differences that underlie variations in flavin reactivity, as well as the reactivities of other heterocyclic cofactors.