Flavin mononucleotide

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Flavin mononucleotide
Skeletal formula of flavin mononucleotide
Ball-and-stick model of the flavin mononucleotide molecule
Names
IUPAC 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 phosphate
Other names
  • FMN
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.005.150 Edit this at Wikidata
E number E101a (colours)
IUPHAR/BPS
MeSH Flavin+mononucleotide
UNII
  • 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 checkY
    Key: FVTCRASFADXXNN-SCRDCRAPSA-N checkY
  • 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
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 checkY☒N ?)

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

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]

Food additive

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

jams, milk products, and sweets and sugar products.[6]

See also

References

  1. PMID 4379862
    .
  2. PMID 9514256
    .
  3. PMID 29643256
    .
  4. S2CID 207990089
    .
  5. ^ "Current EU approved additives and their E Numbers", Food Standards Agency website, retrieved 15 Dec 2011
  6. PMID 32625611
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Flavin_mononucleotide&oldid=1214523336"