Riboflavin, a member of the B vitamin family, is a water-soluble vitamin that participates in energy metabolism processes via two coenzymes, flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD), in oxidized and reduced forms. Low levels of riboflavin have been associated with growth and developmental problems and have been reported in low-income countries due to inadequate intake of meat and dairy products. Thus, the need for a robust and accessible detection kit led to efforts to synthesize the active compound, a flavin derivative able to interact selectively and simultaneously with the riboflavin binding protein (RBP) and the detection system, avidin, at physiological pH. Considering that the biotin-avidin detection system is robust and widely used, and that the RBP – Riboflavin interaction occurs presumably at the flavin moiety, we aimed to connect the two, biotin and flavin, through a spacer, essentially an alkyl chain. The length and functionalization of the chain dictated the rigidity of the compound and distance between the two moieties. The relationship between the connector characteristics and the binding ability of the synthesized compounds to RBP and avidin was investigated.

Detection of riboflavin deficiency: Do we need the ribityl tail?

ACS Spring 2022

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