Alkaline Hydrolysis of Riboflavin

Surrey, Alexander R.; Nachod, Frederick C.

doi:10.1021/ja01149a128

Cited by 40 publications

(29 citation statements)

References 2 publications

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“…In alkaline conditions, FMN is known to exhibit photoinduced electron transfer33 and undergo hydrolysis with OH − at high temperature (353 K)3435. For this reason, we aimed to explore the temporal stability of the FMN-Na redox reaction.…”

Section: Resultsmentioning

confidence: 99%

A biomimetic redox flow battery based on flavin mononucleotide

et al. 2016

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The versatility in design of redox flow batteries makes them apt to efficiently store energy in large-scale applications at low cost. The discovery of inexpensive organic electroactive materials for use in aqueous flow battery electrolytes is highly attractive, but is thus far limited. Here we report on a flow battery using an aqueous electrolyte based on the sodium salt of flavin mononucleotide. Flavins are highly versatile electroactive molecules, which catalyse a multitude of redox reactions in biological systems. We use nicotinamide (vitamin B3) as a hydrotropic agent to enhance the water solubility of flavin mononucleotide. A redox flow battery using flavin mononucleotide negative and ferrocyanide positive electrolytes in strong base shows stable cycling performance, with over 99% capacity retention over the course of 100 cycles. We hypothesize that this is enabled due to the oxidized and reduced forms of FMN-Na being stabilized by resonance structures.

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Section: Resultsmentioning

confidence: 99%

A biomimetic redox flow battery based on flavin mononucleotide

et al. 2016

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“…Evidence for photodegradation in vivo has been obtained for newborns during photo therapy for hyperbilirubinemia (87,216). Heating samples that contain riboflavin in acid may yield 2',5'-anhydro-riboflavin (47) and, in base, 1,2-dihydro-6, 7-dimethyl-2-keto-l -D-ribityl-3-quinoxaline carboxylic acid plus urea (246). The flavin coenzymes are especially susceptible to both chemical and enzymatic hydrolysis to form riboflavin.…”

Section: Chemical and Biological Degradation Productsmentioning

confidence: 99%

Formation and Mode of Action of Flavoproteins

et al. 1981

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“…They degraded lumiflavin (11) in alkaline medium and were able to isolate urea and 1,2dihydro-l,6,$-trin1etliyl-2-keto-3-q~~inoxaline carboxylic acid from the reaction mixture. Other reports including those of Surrey and Nachod (6) substantiated these findings. The first detailed kinetic study on the hydrolysis of riboflavin has been reported by Farrer and MacEwan (7).…”

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confidence: 60%