フラビンモノヌクレオチド

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Flavin mononucleotide/ja
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Flavin mononucleotide/ja
フラビンモノヌクレオチドの骨格式
フラビンモノヌクレオチド分子のボール&スティックモデル
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
MeSH Flavin+mononucleotide
UNII
Properties
C17H21N4O9P
Molar mass 456.344 g/mol
Melting point 195 °C

フラビンモノヌクレオチドFMN)、またはリボフラビン-5′-リン酸は、酵素リボフラビンキナーゼによってリボフラビン(ビタミンB2)から生成される生体分子であり、NADHデヒドロゲナーゼを含む様々な酸化還元酵素補欠基として機能する。触媒サイクルの間、酸化型(FMN)、セミキノン型(FMNH-)、還元型(FMNH2)の可逆的な相互変換が様々な酸化還元酵素で起こる。FMNはNADよりも強い酸化剤であり、1電子移動と2電子移動の両方に関与できるので特に有用である。青色光受容体としての役割において、(酸化)FMNはE/Z異性化ではなく、シグナル伝達状態として「従来の」光受容体より際立っている。

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. 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.

Food additive

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.