fructose-1,6-bisphosphate

フルクトース1,6-ビスリン酸

WordNet

1. a simple sugar found in honey and in many ripe fruits (同)fruit_sugar, levulose, laevulose

PrepTutorEJDIC

1. 〈U〉果糖

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/11 01:04:16」(JST)

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Fructose 1,6-bisphosphate

Identifiers
CAS Number	488-69-7 Y
ChEBI	CHEBI:40595 Y
ChEMBL	ChEMBL1089962 Y
ChemSpider	393165 Y
Jmol 3D model	Interactive image
MeSH	fructose-1,6-diphosphate
PubChem	445557
InChI InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1 Y Key: RNBGYGVWRKECFJ-ZXXMMSQZSA-N Y InChI=1/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1 Key: RNBGYGVWRKECFJ-ZXXMMSQZBN
SMILES O=P(OC[C@]1(O)O[C@@H]([C@@H](O)[C@@H]1O)COP(=O)(O)O)(O)O
Properties
Chemical formula	C6H14O12P2
Molar mass	340.116
Pharmacology
ATC code	C01EB07 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Fructose 1,6-bisphosphate, also known as Harden-Young ester, is fructose sugar phosphorylated on carbons 1 and 6 (i.e., is a fructosephosphate). The β-D-form of this compound is very common in cells. The vast majority of glucose and fructose entering a cell will become converted to fructose 1,6-bisphosphate at some point.

Fructose 1,6-bisphosphate in glycolysis

Fructose 1,6-bisphosphate lies within the glycolysis metabolic pathway and is produced by phosphorylation of fructose 6-phosphate. It is, in turn, broken down into two compounds: glyceraldehyde 3-phosphate and dihydroxyacetone phosphate. It is an allosteric activator of pyruvate kinase through distinct interactions of binding and allostery at the enzyme's catalytic site

β-D-fructose 6-phosphate	6-phosphofructo 1-kinase		β-D-fructose 1,6-bisphosphate	Fructose-bisphosphate aldolase		D-glyceraldehyde 3-phosphate		dihydroxyacetone phosphate
							+
	ATP	ADP
	Pi	H2O
	Hexose diphosphatase			Fructose-bisphosphate aldolase

Compound C05345 at KEGG Pathway Database. Enzyme 2.7.1.11 at KEGG Pathway Database. Enzyme 3.1.3.11 at KEGG Pathway Database. Compound C05378 at KEGG Pathway Database. Enzyme 4.1.2.13 at KEGG Pathway Database. Compound C00111 at KEGG Pathway Database. Compound C00118 at KEGG Pathway Database.

The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.

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

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

File:WP534.png

Glycolysis and Gluconeogenesis edit

Fructose 1,6-bisphosphate isomerism

Main article: Fructose

Fructose 1,6-bisphosphate has only one biologically active isomer, the β-D-form. There are many other isomers, analogous to those of fructose.

Iron Chelation

Fructose 1,6-bis(phosphate) has also been implicated in the ability to bind and sequester Fe(II), a soluble form of iron whose oxidation to the insoluble Fe(III) is capable of generating reactive oxygen species via Fenton chemistry. The ability of fructose 1,6-bis(phosphate) to bind Fe(II) may prevent such electron transfers, and thus act as an antioxidant within the body. Certain neurodegenerative diseases, like Alzheimer's and Parkinson's, have been linked to metal deposits with high iron content, although it is uncertain whether Fenton chemistry plays a substantial role in these diseases, or whether fructose 1,6-bis(phosphate) is capable of mitigating those effects.

See also

• Fructose 2,6-bisphosphate

References

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. 吸収不良の治療の概要 overview of the treatment of malabsorption
• 2. 食事中の炭水化物 dietary carbohydrates
• 3. 幼児および小児における低血糖症の病因 etiology of hypoglycemia in infants and children
• 4. 腸内ガスと膨満 intestinal gas and bloating
• 5. 男性不妊症の評価 evaluation of male infertility

English Journal

• Increased transcript levels and kinetic function of pyruvate kinase during severe dehydration in aestivating African clawed frogs, Xenopus laevis.

• Dawson NJ1, Biggar Y2, Malik AI2, Storey KB3.
• Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology.Comp Biochem Physiol B Biochem Mol Biol.2018 Oct;224:245-252. doi: 10.1016/j.cbpb.2018.01.003. Epub 2018 Jan 10.
• PMID 29331521

• Proteomic and immunomic analysis of Schistosoma mekongi egg proteins.

• Thiangtrongjit T1, Adisakwattana P2, Limpanont Y3, Dekumyoy P4, Nuamtanong S5, Chusongsang P6, Chusongsang Y7, Reamtong O8.
• Experimental parasitology.Exp Parasitol.2018 Aug;191:88-96. doi: 10.1016/j.exppara.2018.07.002. Epub 2018 Jul 17.
• PMID 30009810

• Fructose-1,6-Bisphosphate Prevents Bleomycin-Induced Pulmonary Fibrosis in Mice and Inhibits the Proliferation of Lung Fibroblasts.

• Jost RT1,2, Dias HB3, Krause GC1, de Souza RG3, de Souza TR3, Nuñez NK3, Dos Santos FG2, Haute GV1, da Silva Melo DA1, Pitrez PM3, da Silva VD4, Donadio MVF1,3, de Oliveira JR5.
• Inflammation.Inflammation.2018 Jul 11. doi: 10.1007/s10753-018-0842-3. [Epub ahead of print]
• PMID 29995294

Japanese Journal

• Effects of Taurine Administration on Carbohydrate Metabolism in Skeletal Muscle during the Post-Exercise Phase

• Ｊｏｕｒｎａｌ　ｏｆ　Ｎｕｔｒｉｔｉｏｎａｌ　Ｓｃｉｅｎｃｅ　ａｎｄ　Ｖｉｔａｍｉｎｏｌｏｇｙ　 62(4), 257-264, 2016
• NAID 130005249058

• Absolute quantitation of glycolytic intermediates reveals thermodynamic shifts in Saccharomyces cerevisiae strains lacking PFK1 or ZWF1 genes

• Journal of bioscience and bioengineering 120(3), 280-286, 2015-09
• NAID 110009987505

• Pitfall in the Diagnosis of Fructose-1,6-Bisphosphatase Deficiency: Difficulty in Detecting Glycerol-3-Phosphate with Solvent Extraction in Urinary GC/MS Analysis

• The Tohoku Journal of Experimental Medicine 237(3), 235-239, 2015
• NAID 130005107826

Related Links

• Fructose 1,6-bisphosphateとは - goo Wikipedia (ウィキペディア)

Fructose 1,6-bisphosphate has only one biologically active isomer, the β-D-form. There are many other isomers, analogous to those of fructose. Iron Chelation [edit] Fructose 1,6-bis(phosphate) has also been implicated in the ability to ...

• fructose-1,6-diphosphate | C6H14O12P2 - PubChem

PubChem CID: 10267 Chemical Names: Fructose-1,6-diphosphate; D-Fructose, 1,6-bis(dihydrogen phosphate); CHEBI:28013; Beta-D-Fructose 1,6-bisphosphate; FBP; 1,6-di-O-phosphono-beta-D-fructofuranose; More... Molecular ...

Related Pictures

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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」「アルドラーゼ」「フルクトース6-リン酸」「フルクトース1,6-ビスリン酸」
関連記事	「bisphosphate」「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

「アルドラーゼ」

　　[★]

英

aldolase, ALD

同

フルクトースビスリン酸アルドラーゼ fructose-bisphosphate aldolase

関

アルドース

• first aid step1 2006 p.87,89,93,319

アイソザイム(アルドラーゼアイソザイム)

• aldolase A：筋、赤血球

• FBPに親和性が高い (fructose-1,6-bisphosphate)

• aldolase B：肝臓、腎、小腸　(aldolase B = fructose-1-phosphate aldolase, フルクトース-1-リン酸アルドラーゼ)

• FBPとF1Pを基質にできる (fructose-1-phosphate)

• aldolase C：神経組織

臨床関連

アルドラーゼ欠損症

• ALD Aの異常：遺伝性溶血性貧血
• ALD Bの異常：遺伝性果糖不耐症

「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

「bisphosphate」

　　[★]

二リン酸エステル、二リン酸

関

diphosphate、diphosphoric acid、pyrophosphate

「fructose」

　　[★] フルクトース、果糖、fruit sugar、levulose