What question did this study set out to answer?

This research aims to synthesize cyclic-FMN and establish its presence in biological specimens.

January 23, 2026Biomolecules0 citationsOpen Access

Cyclic-FMN Is a Detectable, Putative Intermediate of FAD Metabolism

LBLuxene BelfleurUSA Mitchell Cancer Institute JKJuha P. KallioUniversity of Bergen WRWito RichterUniversity of South Alabama

Key Points

This research aims to synthesize cyclic-FMN and establish its presence in biological specimens.
Synthesized cFMN from FMN and FAD.
Optimized reaction conditions using equimolar ZnSO4 and FAD.
Conducted stability assessments under acidic and basic conditions.
Detected cFMN using liquid chromatography coupled with mass spectrometry.
Successfully synthesized pure cFMN.
Demonstrated cFMN stability in varying pH conditions.
Detected cFMN in biological samples, addressing underreporting issues.

Abstract

Free flavin adenine dinucleotide (FAD) is metabolized to flavin mononucleotide (FMN) and adenine monophosphate (AMP) by hydrolases and to 4′,5′-cyclic phosphoriboflavin (cFMN) and AMP by the triose kinase FMN cyclase (TKFC). Yet, the lack of analytical standards for cFMN might have resulted in the incidence of cFMN in biological specimens being underreported. To address this shortcoming, cFMN was synthesized from either FMN or FAD. The optimization of the FAD to cFMN reaction conditions revealed that an equimolar ratio of ZnSO4 and FAD yielded pure cFMN upon the precipitation of AMP-Zn salts. cFMN is stable to aqueous acidic and basic conditions and is readily extracted from biological samples for detection by liquid chromatography coupled with mass spectrometry. Although cFMN is hydrolyzed by liver tissue extracts to FMN and riboflavin, the mechanisms for this conversion remain elusive.

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