flavin mononucleotide

フラビンモノヌクレオチド FMN

WordNet

1. a ketone that forms the nucleus of certain natural yellow pigments like riboflavin

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/06 23:56:02」(JST)

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Flavin mononucleotide

Names
Other names FMN
Identifiers
CAS Number	146-17-8 Y
ChEBI	CHEBI:17621 Y
ChEMBL	ChEMBL1201794 N
ChemSpider	559060 Y
IUPHAR/BPS	5185
Jmol interactive 3D	Image
MeSH	Flavin+mononucleotide
PubChem	643976
UNII	7N464URE7E Y
InChI 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 Y Key: FVTCRASFADXXNN-SCRDCRAPSA-N Y InChI=1/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 Key: FVTCRASFADXXNN-SCRDCRAPBE
SMILES Cc1cc2c(cc1C)n(c-3nc(=O)[nH]c(=O)c3n2)C[C@@H]([C@@H]([C@@H](COP(=O)(O)O)O)O)O
Properties
Chemical formula	C17H21N4O9P
Molar mass	456.344 g/mol
Melting point	195 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B₂) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue-light photo receptors. 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.

Food additiveEdit

Flavin mononucleotide is also used as an orange-red food colour additive, designated in Europe as E number E101a.

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.

See alsoEdit

• FAD

ReferencesEdit

External linksEdit

• FMN in the EBI Macromolecular Structure Database

UpToDate Contents

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English Journal

• Determination of free and bound riboflavin in cow's milk using a novel flavin-binding protein.

• Koop J, Monschein S, Pauline Macheroux E, Knaus T, Macheroux P.SourceInstitute of Biochemistry, Graz University of Technology, A-8010 Graz, Austria.
• Food chemistry.Food Chem.2014 Mar 1;146:94-7. doi: 10.1016/j.foodchem.2013.09.026. Epub 2013 Sep 12.
• A recently described putative protease from the gut bacterium Bacteroides thetaiotaomicron (termed ppBat) exhibits two tryptophan residues in the interface which enable specific binding of the isoalloxazine heterocycle of riboflavin and its two cofactor forms, FMN and FAD. Recombinant ppBat was used
• PMID 24176318

• A hybrid FLIM-elastic net platform for label free profiling of breast cancer.

• Damayanti NP, Craig AP, Irudayaraj J.SourceDepartment of Agricultural and Biological Engineering and Bindley Bioscience Center, 225 S. University Street, West Lafayette, IN, USA.
• The Analyst.Analyst.2013 Dec 7;138(23):7127-34. doi: 10.1039/c3an01097j.
• We report a label-free fluorescence lifetime profiling strategy to classify breast cancer cells, MCF10CA1h (malignant), MCF10A (nonmalignant), and MCF10AneoT (premalignant) in different stages of malignancy. Fluorescence Lifetime Imaging Microscopy (FLIM) was used to record the lifetime of autofluor
• PMID 24106733

• Nitric oxide synthase inhibition and oxidative stress in cardiovascular diseases: Possible therapeutic targets?

• Rochette L, Lorin J, Zeller M, Guilland JC, Lorgis L, Cottin Y, Vergely C.SourceLaboratoire de Physiopathologie et Pharmacologies Cardio-Métaboliques (LPPCM), France. Electronic address: luc.rochette@u-bourgogne.fr.
• Pharmacology & therapeutics.Pharmacol Ther.2013 Dec;140(3):239-57. doi: 10.1016/j.pharmthera.2013.07.004. Epub 2013 Jul 13.
• Nitric oxide (NO) is synthetized enzymatically from l-arginine (l-Arg) by three NO synthase isoforms, iNOS, eNOS and nNOS. The synthesis of NO is selectively inhibited by guanidino-substituted analogs of l-Arg or methylarginines such as asymmetric dimethylarginine (ADMA), which results from protein
• PMID 23859953

Japanese Journal

• Solution Chemical Synthesis of Hollow Vaterite Polycrystalline Particles for Advanced Biomaterial Applications

• Sugiura Yuki,Onuma Kazuo,Yamazaki Atsushi
• Chemistry Letters, 2014
• … Starting materials consist of CaCl2, NaHCO3, NaCl, and a flavin mononucleotide—a vitamin B2 derivative. …
• NAID 130004693844

• A Key Factor for Ultrafast Rates of Photoinduced Electron Transfer among Five Flavin Mononucleotide Binding Proteins : Effect of Negative, Positive, and Neutral Charges at Residue 13 on the Rate

• TANIGUCHI Seiji,CHOSROWJAN Haik,TANAKA Fumio,NAKANISHI Takeshi,SATO Shuta,HARUYAMA Yoshihiro,KITAMURA Masaya
• Bulletin of the Chemical Society of Japan 86(3), 339-350, 2013-03-15
• NAID 10031162139

• Selected Papers : A Key Factor for Ultrafast Rates of Photoinduced Electron Transfer among Five Flavin Mononucleotide Binding Proteins : Effect of Negative, Positive, and Neutral Charges at Residue 13 on the Rate

• Taniguchi Seiji,Chosrowjan Haik,Tanaka Fumio [他]
• Bulletin of the Chemical Society of Japan 86(3), 339-350, 2013-03
• NAID 40019609049

Related Links

• Flavin mononucleotide | definition of flavin mononucleotide by ...

flavin [fla´vin] any of a group of water-soluble yellow pigments widely distributed in animals and plants, including riboflavin and yellow enzymes. flavin adenine dinucleotide (FAD) a coenzyme that is a condensation product of riboflavin ...

• Flavin-mononucleotide | Define Flavin-mononucleotide at ...

flavin mononucleotide or flavine mononucleotide n. Abbr. FMN A derivative of riboflavin that condenses with adenine nucleotide to form flavin adenine dinucleotide and that acts as a coenzyme of various flavoproteins.

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リンク元	「フラビンモノヌクレオチド」

「フラビンモノヌクレオチド」

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英

flavin mononucleotide, FMN

関

フラビン、フラビンアデニンジヌクレオチド