fructose 6-phosphate

フルクトース6-リン酸

WordNet

1. a salt of phosphoric acid (同)orthophosphate, inorganic_phosphate
2. carbonated drink with fruit syrup and a little phosphoric acid
3. a simple sugar found in honey and in many ripe fruits (同)fruit_sugar, levulose, laevulose

PrepTutorEJDIC

1. 〈U〉リン酸塩 / 《複数形で》リン酸肥料
2. 〈U〉果糖

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/23 11:52:09」(JST)

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[Wiki en表示]

Fructose 6-phosphate

Names
IUPAC names [(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 Registry Number	643-13-0 Y
Abbreviations	F6P
ChEBI	CHEBI:16084 N
ChemSpider	392657 Y
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
Jmol-3D images	Image
PubChem	444848
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: Y/N?)
Infobox references

Fructose 6-phosphate (also known as the Neuberg ester) is fructose sugar phosphorylated on carbon 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 this at some point. The name Neuberg ester comes from the German biochemist Carl Neuberg.

History

In 1918, Carl Neuberg found that the compound (only later identified as fructose 6-phosphate) could be produced by mild acid hydrolysis of "Harden-Young ester" (fructose 2,6-bisphosphate).

Fructose 6-phosphate 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]]

File:WP534.png

Glycolysis and Gluconeogenesis edit

See also

• Mannose phosphate isomerase

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. カルシウムおよびリン酸バランスの調節 regulation of calcium and phosphate balance
• 2. 低リン血症の原因 causes of hypophosphatemia
• 3. 高リン血症の原因および治療の概要 overview of the causes and treatment of hyperphosphatemia
• 4. 慢性腎疾患における高リン血症の治療 treatment of hyperphosphatemia in chronic kidney disease
• 5. 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

English Journal

• Isolation and characterization of a mutant defective in triacylglycerol accumulation in nitrogen-starved Chlamydomonas reinhardtii.

• Hung CH1, Kanehara K2, Nakamura Y3.
• Biochimica et biophysica acta.Biochim Biophys Acta.2016 Apr 7. pii: S1388-1981(16)30089-0. doi: 10.1016/j.bbalip.2016.04.001. [Epub ahead of print]
• Triacylglycerol (TAG), a major source of biodiesel production, accumulates in nitrogen-starved Chlamydomonas reinhardtii. However, the metabolic pathway of starch-to-TAG conversion remains elusive because an enzyme that affects the starch degradation is unknown. Here, we isolated a new class of muta
• PMID 27060488

• T-to-R switch of muscle fructose-1,6-bisphosphatase involves fundamental changes of secondary and quaternary structure.

• Barciszewski J1, Wisniewski J2, Kolodziejczyk R3, Jaskolski M1, Rakus D2, Dzugaj A4.
• Acta crystallographica. Section D, Structural biology.Acta Crystallogr D Struct Biol.2016 Apr 1;72(Pt 4):536-50. doi: 10.1107/S2059798316001765. Epub 2016 Mar 30.
• Fructose-1,6-bisphosphatase (FBPase) catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate and is a key enzyme of gluconeogenesis and glyconeogenesis and, more generally, of the control of energy metabolism and glucose homeostasis. Vertebrates, and notably Homo sapiens, expre
• PMID 27050133

• Novel mode of inhibition by D-tagatose 6-phosphate through a Heyns rearrangement in the active site of transaldolase B variants.

• Stellmacher L1, Sandalova T2, Schneider S1, Schneider G3, Sprenger GA1, Samland AK1.
• Acta crystallographica. Section D, Structural biology.Acta Crystallogr D Struct Biol.2016 Apr 1;72(Pt 4):467-76. doi: 10.1107/S2059798316001170. Epub 2016 Mar 24.
• Transaldolase B (TalB) and D-fructose-6-phosphate aldolase A (FSAA) from Escherichia coli are C-C bond-forming enzymes. Using kinetic inhibition studies and mass spectrometry, it is shown that enzyme variants of FSAA and TalB that exhibit D-fructose-6-phosphate aldolase activity are inhibited covale
• PMID 27050126

Japanese Journal

• Modulation of Allosteric Regulation by E38K and G101N Mutations in the Potato Tuber ADP-glucose Pyrophosphorylase

• WAKUTA Shinji,SHIBATA Yumi,YOSHIZAKI Yumiko,SABURI Wataru,HAMADA Shigeki,ITO Hiroyuki,HWANG Seon-Kap,OKITA Thomas W.,MATSUI Hirokazu
• Bioscience, Biotechnology, and Biochemistry, 2013
• … The higher plant ADP-glucose (ADPG) pyrophosphorylase (AGPase), composed of two small subunits and two large subunits (LSs), produces ADPG, the sole substrate for starch biosynthesis from α-D-glucose 1-phosphate and ATP. …
• NAID 130003361219

• 1つの酵素が2つの反応を触媒するしくみ

• 西増 弘志,伏信 進矢,若木 高善
• 日本結晶学会誌 54(2), 113-118, 2012-04-30
• … Unlike ordinary enzymes, fructose-1,6-bisphosphate (FBP) aldolase/phosphatase (FBPA/P) catalyzes two distinct reactions : (1) the aldol condensation of dihydroxyacetone phosphate (DHAP) and glyceraldehyde-3-phosphate to FBP, and (2) the dephosphorylation of FBP to fructose-6-phosphate. …
• NAID 10030631990

• 乳酸菌由来糖質加水分解酵素ファミリー32タンパク質の基質認識機構の解明

• 中井 博之,SVENSSON Birte,大坪 研一,中井 博之,Svensson Birte,大坪 研一
• 新潟大学農学部研究報告 64(2), 115-126, 2012-03-00
• … Two fructo-oligosaccharide active enzymes, BfrA and ScrB, of glycoside hydrolase family 32 are found inLactobacillus acidophilus NCFM and belong to phylogenetic clusters of bacterial β-fructosidase and sucrose 6-phosphatehydrolase, respectively, involved in the intracellular metabolism of kesto-oligosaccharides [β-D-fructofuranosyl-(2,1)]n-β-D-fructofuranosyl-(2,1)-α-D-glucopyranose (n, 1-3) and sucrose. …
• NAID 120005239946

Related Links

• fructose 6-phosphate - definition of fructose 6-phosphate by ...

fructose a hexose sugar found in honey and many sweet fruits; called also levulose and fruit sugar. It is used in solution as a fluid and nutrient replenisher. fructose 1,6-bisphosphatase key regulatory enzyme of gluconeogenesis.

• Fructose 6-phosphate definition of Fructose 6-phosphate in ...

We developed a sensitive liquid chromatography-tandem mass spectrometry (LC-MS/ MS) method to simultaneously analyze the intracellular sugar phosphates dihydroxyacetone phosphate (DHAP), glyceraldehyde 3-phosphate ...

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★リンクテーブル★

リンク元	「解糖系」「フルクトース6-リン酸」「F6P」
拡張検索	「glutamine-fructose-6-phosphate transaminase」「fructose-6-phosphate」
関連記事	「phosphate」「fructose」

「解糖系」

　　[★]

英

glycolytic pathway

同

エムデン-マイヤーホフ経路 Embden-Meyerhof pathway

関

解糖、TCA回路

• CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2OH)H-O- グルコース (OHが↓↓↑↓↑)
• CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- グルコース-6-リン酸 (OHが↓↓↑↓↑)
• C(CH2OH)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-6-リン酸
• C(CH2O-PO3)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-1,6-リン酸

glucose
↓-hexokinase/glucokinase(liver)
glucose 6-phosphate
↓-phosphohexose isomerase
fructose 6-phosphate
↓-phosphofructokinase
fructose 1,6-bisphosphate
↓-aldolase
glyceraldehyde 3-phosphate
↓-glyceraldehyde-3-phosphate dehydrogenase
1,3-bisphosphoglycerate
↓-phosphoglycerate kinase →ATP
3-phosphoglycerate
↓-phosphoglyceate mutase
2-phosphoglycerate
↓-enolase
phosphoenolpyruvate
↓-pyruvate kinase → ATP
pyruvate
　－(pyruvate dehydrogenase)→acetyl-CoA
　－(pyruvate carboxylase)→oxaloacetate－(NADH+H+)→malate

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解糖系の酵素 (first aid step1 2006 p.87, FASTEP1_87_酵素一覧.xls)

1	galactokinase	キナーゼ
2	galactose-1-phosphate uridyltransferase	転移酵素
3	hexokinase/glucokinase	キナーゼ
4	glucose-6-phosphatase	ホスファターゼ
5	glucose-6-phosphate dehydrogenase	脱水素酵素
6	transketolase
7	phosphofructokinase	キナーゼ
8	fructose-1,6-bisphosphatase	ホスファターゼ
9	fructokinase	キナーゼ	フルクトキナーゼ
10	aldolase B		アルドラーゼ
11	pyruvate kinase	キナーゼ	ピルビン酸キナーゼ
12	pyruvate dehydrogenase	脱水素酵素	ピルビン酸デヒドロゲナーゼ
13	HMG-CoA reductase	還元酵素	HMG-CoA還元酵素
14	pyruvate carboxylase	カルボキシラーゼ	ピルビン酸カルボキシラーゼ
15	PEP carboxykinase	キナーゼ	PEPカルボキシキナーゼ
16	citrate synthase	合成酵素	クエン酸合成酵素
17	α-ketoglutarate dehydrogenase	脱水素酵素	α-ケトグルタミン酸脱水素酵素
18	ornithine transcarbamylase	転移酵素	オルニチンカルバモイルトランスフェラーゼ

「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

「F6P」

　　[★] フルクトース6-リン酸

同

fructose 6-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

「fructose-6-phosphate」

　　[★] フルクトース6-リン酸

「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