Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as the prosthetic group of various oxidoreductases, including NADH dehydrogenase, as well as cofactor in biological blue-light photo receptors.[1] During the catalytic cycle, a reversible interconversion of the oxidized (FMN), semiquinone (FMNH•), and reduced (FMNH2) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. In its role as blue-light photo receptor, (oxidized) FMN stands out from the 'conventional' photo receptors as the signaling state and not an E/Z isomerization.
It is the principal form in which riboflavin is found in cells and tissues. It requires more energy to produce, but is more soluble than riboflavin. In cells, FMN occurs freely circulating but also in several covalently bound forms.[2] Covalently or non-covalently bound FMN is a cofactor of many enzymes playing an important pathophysiological role in cellular metabolism. For example dissociation of flavin mononucleotide from mitochondrial complex I has been shown to occur during ischemia/reperfusion brain injury during stroke.[3][4]
Flavin mononucleotide is also used as an orange-red food colour additive, designated in Europe as E number E101a.[5]
E106, a very closely related food dye, is riboflavin-5′-phosphate sodium salt, which consists mainly of the monosodiumsalt of the 5′-monophosphate ester of riboflavin. It is rapidly turned to free riboflavin after ingestion. It is found in many foods for babies and young children as well as jams, milk products, and sweets and sugar products.[6]
^Tsibris, John C. M.; McCormick, Donald B.; Wright, Lemuel D. (1966). "Studies on the Binding and Function of Flavin Phosphates with Flavin Mononucleotide-dependent Enzymes". Journal of Biological Chemistry. 241 (5): 1138–43. doi:10.1016/S0021-9258(18)96813-4. PMID 4379862.
^Mewies M, McIntire WS, Scrutton NS (1998). "Covalent attachment of flavin adenine dinucleotide (FAD) and flavin mononucleotide (FMN) to enzymes: The current state of affairs". Protein Science. 7 (1): 7–20. doi:10.1002/pro.5560070102. PMC2143808. PMID 9514256.
^Kahl, A; Stepanova, A; Konrad, C; Anderson, C; Manfredi, G; Zhou, P; Iadecola, C; Galkin, A (2018). "Critical Role of Flavin and Glutathione in Complex I-Mediated Bioenergetic Failure in Brain Ischemia/Reperfusion Injury". Stroke. 49 (5): 1223–1231. doi:10.1161/STROKEAHA.117.019687. PMC5916474. PMID 29643256.
^Galkin, A (2019). "Brain Ischemia/Reperfusion Injury and Mitochondrial Complex I Damage". Biochemistry. Biokhimiia. 84 (11): 1411–1423. doi:10.1134/S0006297919110154. PMID 31760927. S2CID 207990089.
^"Current EU approved additives and their E Numbers", Food Standards Agency website, retrieved 15 Dec 2011
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Flavin mononucleotide FMN or riboflavin 5 phosphate is a biomolecule produced from riboflavin vitamin B2 by the enzyme riboflavin kinase and functions as the prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue light photo receptors 1 During the catalytic cycle a reversible interconversion of the oxidized FMN semiquinone FMNH and reduced FMNH2 forms occurs in the various oxidoreductases FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one and two electron transfers In its role as blue light photo receptor oxidized FMN stands out from the conventional photo receptors as the signaling state and not an E Z isomerization Flavin mononucleotide NamesIUPAC name 1 Deoxy 1 7 8 dimethyl 2 4 dioxo 3 4 dihydrobenzo g pteridin 10 2H yl D ribitol 5 dihydrogen phosphate Systematic IUPAC name 2R 3S 4S 5 7 8 Dimethyl 2 4 dioxo 3 4 dihydrobenzo g pteridin 10 2H yl 2 3 4 trihydroxypentyl dihydrogen phosphateOther names FMNIdentifiersCAS Number 146 17 8 Y130 40 5 sodium salt Y3D model JSmol Interactive imageChEBI CHEBI 17621 YChEMBL ChEMBL1201794 NChemSpider 559060 YECHA InfoCard 100 005 150E number E101a colours IUPHAR BPS 5185MeSH Flavin mononucleotidePubChem CID 643976UNII 7N464URE7E YCompTox Dashboard EPA DTXSID8023559InChI InChI 1S C17H21N4O9P c1 7 3 9 10 4 8 7 2 21 15 13 18 9 16 25 20 17 26 19 15 5 11 22 14 24 12 23 6 30 31 27 28 29 h3 4 11 12 14 22 24H 5 6H2 1 2H3 H 20 25 26 H2 27 28 29 t11 12 14 m0 s1 YKey FVTCRASFADXXNN SCRDCRAPSA N YSMILES Cc1cc2c cc1C n c 3nc O nH c O c3n2 C C H C H C H COP O O O O O OPropertiesChemical formula C17H21N4O9PMolar mass 456 344 g molMelting point 195 CExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references This article needs additional citations for verification Please help improve this article by adding citations to reliable sources Unsourced material may be challenged and removed Find sources Flavin mononucleotide news newspapers books scholar JSTOR December 2009 Learn how and when to remove this template message It is the principal form in which riboflavin is found in cells and tissues It requires more energy to produce but is more soluble than riboflavin In cells FMN occurs freely circulating but also in several covalently bound forms 2 Covalently or non covalently bound FMN is a cofactor of many enzymes playing an important pathophysiological role in cellular metabolism For example dissociation of flavin mononucleotide from mitochondrial complex I has been shown to occur during ischemia reperfusion brain injury during stroke 3 4 Contents 1 Food additive 2 See also 3 References 4 External linksFood additive editFlavin mononucleotide is also used as an orange red food colour additive designated in Europe as E number E101a 5 E106 a very closely related food dye is riboflavin 5 phosphate sodium salt which consists mainly of the monosodium salt of the 5 monophosphate ester of riboflavin It is rapidly turned to free riboflavin after ingestion It is found in many foods for babies and young children as well as jams milk products and sweets and sugar products 6 See also editFlavin adenine dinucleotideReferences edit Tsibris John C M McCormick Donald B Wright Lemuel D 1966 Studies on the Binding and Function of Flavin Phosphates with Flavin Mononucleotide dependent Enzymes Journal of Biological Chemistry 241 5 1138 43 doi 10 1016 S0021 9258 18 96813 4 PMID 4379862 Mewies M McIntire WS Scrutton NS 1998 Covalent attachment of flavin adenine dinucleotide FAD and flavin mononucleotide FMN to enzymes The current state of affairs Protein Science 7 1 7 20 doi 10 1002 pro 5560070102 PMC 2143808 PMID 9514256 Kahl A Stepanova A Konrad C Anderson C Manfredi G Zhou P Iadecola C Galkin A 2018 Critical Role of Flavin and Glutathione in Complex I Mediated Bioenergetic Failure in Brain Ischemia Reperfusion Injury Stroke 49 5 1223 1231 doi 10 1161 STROKEAHA 117 019687 PMC 5916474 PMID 29643256 Galkin A 2019 Brain Ischemia Reperfusion Injury and Mitochondrial Complex I Damage Biochemistry Biokhimiia 84 11 1411 1423 doi 10 1134 S0006297919110154 PMID 31760927 S2CID 207990089 Current EU approved additives and their E Numbers Food Standards Agency website retrieved 15 Dec 2011 Turck Dominique Bresson Jean Louis Burlingame Barbara et al 2017 Dietary Reference Values for riboflavin EFSA Journal 15 8 e04919 doi 10 2903 j efsa 2017 4919 PMC 7010026 PMID 32625611 External links editFMN in the EBI Macromolecular Structure Database Retrieved from https en wikipedia org w index php title Flavin mononucleotide amp oldid 1152636172, wikipedia, wiki, book, books, library,
