fructose-6-phosphate

フルクトース6-リン酸

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2019/06/02 18:46:32」(JST)

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Fructose 6-phosphate

Names
IUPAC name [(2R,3R,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxyphosphonic acid
Other names β-D-fructose 6-phosphate, fructose 6-phosphate
Identifiers
CAS Number	643-13-0 Y
3D model (JSmol)	Interactive image
Abbreviations	F6P
ChEBI	CHEBI:16084 N
ChemSpider	392657 Y
PubChem CID	444848
InChI InChI=1S/C6H13O9P/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6+/m1/s1 Y Key: BGWGXPAPYGQALX-ZXXMMSQZSA-N Y InChI=1/C6H13O9P/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6+/m1/s1 Key: BGWGXPAPYGQALX-ZXXMMSQZBI
SMILES O=P(O)(O)OC[C@H]1O[C@@](O)(CO)[C@@H](O)[C@@H]1O
Properties
Chemical formula	C6H13O9P
Molar mass	260.14 g/mol
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

Fructose 6-phosphate (sometimes called the Neuberg ester) is a derivative of fructose, which has been phosphorylated at the 6-hydroxy group. It is one of several possible fructosephosphates. The β-D-form of this compound is very common in cells. The great majority of glucose and fructose is converted to fructose 6-phosphate upon entering a cell.

History

The name Neuberg ester comes from the German biochemist Carl Neuberg. In 1918, he found that the compound (later identified as fructose 6-phosphate) was beproduced by mild acid hydrolysis of fructose 2,6-bisphosphate.

In glycolysis

Fructose 6-phosphate lies within the glycolysis metabolic pathway and is produced by isomerisation of glucose 6-phosphate. It is in turn further phosphorylated to fructose-1,6-bisphosphate.

α-D-glucose 6-phosphate	Phosphoglucose isomerase		β-D-fructose 6-phosphate	Phosphofructokinase-1		β-D-fructose 1,6-bisphosphate
				ATP	ADP
				Pi	H2O
	Phosphoglucose isomerase			Fructose bisphosphatase

Compound C00668 at KEGG Pathway Database. Enzyme 5.3.1.9 at KEGG Pathway Database. Compound C05345 at KEGG Pathway Database. Enzyme 2.7.1.11 at KEGG Pathway Database. Enzyme 3.1.3.11 at KEGG Pathway Database. Reaction [1] at KEGG Pathway Database. Compound C05378 at KEGG Pathway Database.

Click on genes, proteins and metabolites below to link to respective articles.

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|{{{bSize}}}px|alt=Glycolysis and Gluconeogenesis edit]]

Glycolysis and Gluconeogenesis edit

See also

• Mannose phosphate isomerase

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

• 1. 成人における再発性カルシウム結石の予防prevention of recurrent calcium stones in adults [show details]
  …phytate may be beneficial. In addition, decreasing the intake of oxalate, animal protein, sucrose, fructose, sodium, supplemental vitamin C, and supplemental calcium (as opposed to dietary calcium) may reduce …
• 2. 低リン血症の評価および治療evaluation and treatment of hypophosphatemia [show details]
  …required. If so, the same approach may be reapplied. Oral phosphate supplements (tablets and powders) contain varying ratios of sodium and potassium phosphate. Serious medication errors have occurred due to confusion …
• 3. 急性リン酸腎症acute phosphate nephropathy [show details]
  …following the use of bowel purgatives that contain oral sodium phosphate (OSP) and has been reported following the administration of sodium phosphate-containing enemas . OSP was formerly sold without prescription …
• 4. 大腸内視鏡検査を受ける成人への前処置bowel preparation before colonoscopy in adults [show details]
  … preparations for flexible sigmoidoscopy include two sodium phosphate enemas or two tap water enemas given at least one hour before the procedure . Sodium phosphate enemas should be avoided in older adults or patients …
• 5. 低リン血症の原因causes of hypophosphatemia [show details]
  … manifestations: Mutations in the sodium-phosphate cotransporter gene SLC34A3 produce striking dysfunction of the type 2c sodium-phosphate cotransporter and lead to hereditary… and hereditary fructose intolerance are the most common causes of this syndrome.…

English Journal

• Effects of lead exposure on brain glucose metabolism and insulin signaling pathway in the hippocampus of rats.

• Yun S, Wu Y, Niu R, Feng C, Wang J.
• Toxicology letters. 2019 Aug;310()23-30.
• The aim of this study was to determine whether Pb affects glucose metabolism in the hippocampus of rats. Male Sprague-Dawley rats aged 21 days were orally administered a 0.1%, 0.2%, or 0.3% lead acetate solution in deionized water for 65 days. Then, the weight of the rats; brain Pb content; brain gl
• PMID 30980912

• Crystal structure of a xylulose 5-phosphate phosphoketolase. Insights into the substrate specificity for xylulose 5-phosphate.

• Scheidig AJ, Horvath D, Szedlacsek SE.
• Journal of structural biology. 2019 Jul;207(1)85-102.
• Phosphoketolases (PK) are TPP-dependent enzymes which play essential roles in carbohydrate metabolism of numerous bacteria. Depending on the substrate specificity PKs can be subdivided into xylulose 5-phosphate (X5P) specific PKs (XPKs) and PKs which accept both X5P and fructose 6-phosphate (F6P) (X
• PMID 31059775

• Genome-wide identification, expression and functional analysis of the phosphofructokinase gene family in Chinese white pear (Pyrus bretschneideri).

• Lü H, Li J, Huang Y, Zhang M, Zhang S, Wu J.
• Gene. 2019 Jun;702()133-142.
• Phosphofructokinase plays an essential role in sugar metabolism in plants. Plants possess two types of phosphofructokinase proteins for phosphorylation of fructose-6-phosphate, the pyrophosphate-dependent fructose-6-phosphate phosphotransferase (PFP), and the ATP-dependent phosphofructokinase (PFK).
• PMID 30904717

Japanese Journal

• Light/dark cycling causes delayed lipid accumulation and increased photoperiod-based biomass yield by altering metabolic flux in oleaginous Chlamydomonas sp.

• Kato Yuichi,Fujihara Yusuke,Vavricka Christopher J.,Chang Jo-Shu,Hasunuma Tomohisa,Kondo Akihiko
• Biotechnology for Biofuels (12), 39, 2019-02-21
• … Metabolomic analysis revealed accumulation of phosphoenolpyruvate and decrease of glycerol 3-phosphate under the LD condition, suggesting that the imbalance of these metabolites is a source of delayed lipid accumulation. …
• NAID 120006599091

• 日本獸醫學雜誌(The Japanese Journal of Veterinary Science)

• KANAI Shuichiro,SHIMADA Takuro,NARITA Takanori,OKABAYASHI Ken
• Ｔｈｅ　Ｊｏｕｒｎａｌ　ｏｆ　Ｖｅｔｅｒｉｎａｒｙ　Ｍｅｄｉｃａｌ　Ｓｃｉｅｎｃｅ, 2019
• … <p>Phosphofructokinase-1 (EC:2.7.1.11, PFK-1) catalyzes the phosphorylation of fructose 6-phosphate to fructose 1,6-bisphosphate using adenosine triphosphate and is a key regulatory enzyme of glycolysis. …
• NAID 130007620425

• ウンシュウミカン茎における着果が低分子物質に及ぼす影響

• 西川 芙美恵,岩崎 光徳,深町 浩 [他],松本 光
• The Horticulture Journal 85(1), 23-29, 2016
• … デニンジヌクレオチドリン酸（NADPH, NADP⁺），アスコルビン酸といった他の補酵素も着果量の少ない樹に多く含まれていた．さらに，着果少樹は，フルクトース 6 リン酸やリブロース 1,5 リン酸，グルコース 6 リン酸といった糖リン酸を蓄積していた．一方，多くのアミノ酸が，着果過多樹で蓄積していた．これらの結果は，着果が春枝の茎における補酵素や糖，アミノ酸の代謝に影 …
• NAID 130005121328

Related Links

• D-Fructose 6-phosphate disodium salt hydrate ≥98% ...

D-Fructose 6-phosphate disodium salt hydrate ≥98%, amorphous powder; CAS Number: 26177-86-6 (anhydrous); Linear Formula: C6H11Na2O9P · xH2O; find Sigma-Aldrich-F3627 MSDS, related peer-reviewed papers, technical ...

• D-Fructose 6-phosphate hydrate disodium salt (CAS: 26177 ...

AdipoGen社のD-Fructose 6-phosphate hydrate disodium salt (CAS: 26177-86-6)です。AdipoGen社は高品質な低分子化合物，希少な抗生物質，天然物などを販売しています。生理活性や阻害効果を有する物質も多数取り揃えております。

• D-フルクトース6-りん酸二ナトリウム D-Fructose 6-Phosphate ...

富士フイルム和光純薬株式会社は、試験研究用試薬・抗体の製造販売および各種受託サービスを行っています。先端技術の研究から、ライフサイエンス関連、有機合成用や環境測定用試薬まで、幅広い分野で多種多様なニーズに応えて ...

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★リンクテーブル★

リンク元	「グルコース6-リン酸」「ホスホフルクトキナーゼ」「フルクトース6-リン酸」「フルクトース1,6-ビスリン酸」
拡張検索	「glutamine-fructose-6-phosphate transaminase」
関連記事	「phosphate」「fructose」

「グルコース6-リン酸」

　　[★]

英

glucose 6-phosphate, G6P, G-6-P

同

グルコース-6-リン酸 glucose-6-phosphate

関

グルコース1-リン酸、グルコース、解糖系、糖新生

グルコース6-リン酸の運命(G6P) (FB.451)

1. グルコース
2. グリコーゲン
3. リボース5-リン酸(R5P)
4. アセチルCoA

解糖

• glucose－→glucose-6-phosphate

酵素

• 筋肉：glucokinase
• 肝臓：hexokinase

• glucose-6-phosphate－(phosphohexose isomerase)→fructose-6-phosphate

グリコーゲン分解

• glycogen－([[]])→glucose 1-phosphate－([[]])→glucose 6-phosphate

糖新生

• fructose-1,6-bisphosphate－(fructose-1,6-bisphosphatase)→fructose-6-phosphate←([[]])→glucose-6-phosphate－(glucose-6-phosphatase)→glucose

臨床関連

• グルコース-6-リン酸脱水素酵素欠損症

• glucose-6-phosphate dehydrogenaseの欠損による

• フォン・ギールケ病

• glucose-6-phosphataseの欠損による

「ホスホフルクトキナーゼ」

　　[★]

英

phosphofructokinase, PFK

同

ホスホフルクトキナーゼ1 phosphofructokinase-1

関

ホスホフルクトキナーゼ2。解糖系

生体内での調節

乳酸アシドーシスにおいて

• 重炭酸Naの投与でアシドーシスを補正する場合、HCO3-はphosphofructokinaseの活性を亢進させるので、乳酸アシドーシスを悪化させることがある。

急性呼吸性アルカローシスにいて

• 血液のpHが上昇するとホスホフルクトキナーゼの活性が亢進するため、血液中のリン酸が細胞内に取り込まれる結果、低リン血症を来すことがある。

解糖系

• fructose-6-phosphate－(phosphofructokinase)→fructose-1,6-bisphosphate

臨床関連

• 糖原病 垂井病

「フルクトース6-リン酸」

　　[★]

英

fructose6-phosphate, F6P, fructose 6-phosphate

同

フルクトース6リン酸、フルクトース一リン酸 fructose monophosphate

関

解糖系

• glucose-6-phosphate－(phosphohexose isomerase)→fructose-6-phosphate

• fructose-6-phosphate－(phosphofructokinase)→fructose-1,6-bisphosphate

「フルクトース1,6-ビスリン酸」

　　[★]

英

fructose 1,6-bisphosphate FBP

同

フルクトース1,6-二リン酸 fructose 1,6-diphosphate

関

[[]]

解糖系

• fructose-6-phosphate－(phosphofructokinase)→fructose-1,6-bisphosphate

• fructose-1,6-bisphosphate－(aldolase)→glyceraldehyde 3-phosphate + dihydroxyacetone phosphate

「glutamine-fructose-6-phosphate transaminase」

　　[★]

グルタミン・フルクトース-6-リン酸トランスアミナーゼ

「phosphate」

　　[★]

• n.

• (化合物)リン酸塩、リン酸エステル、ホスフェート、フォスフェート、リン酸

関

inorganic phosphate、orthophosphate、orthophosphoric acid、phospho、phosphoester、phosphoric、phosphoric acid、phosphoric acid ester、phosphorus

　 　 　

「fructose」

　　[★] フルクトース、果糖、fruit sugar、levulose