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Revision as of 17:37, 11 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chem...← Previous edit		Latest revision as of 06:39, 2 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits Fixes image on dark mode
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	{{chembox		{{chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 430485181		| verifiedrevid = 470454308
	| ImageFile = beta-D-fructose-6-phosphate_wpmp.png		| ImageFile = beta-D-fructose-6-phosphate_wpmp.png
			| ImageClass = skin-invert
		⚫	| ImageFile2= Fructose 6-phosphate.png
	| ImageSize = 150px		| ImageSize = 150px
			| IUPACName = 6-''O''-Phosphono-α-<small>D</small>-fructofuranose
	| IUPACName = <br>methoxyphosphonic acid
	| OtherNames = β-D-fructose 6-phosphate, <br>fructose 6-phosphate		| OtherNames = β-D-fructose 6-phosphate, <br>fructose 6-phosphate
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
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	| EINECS =		| EINECS =
	| PubChem = 444848		| PubChem = 444848
			| KEGG = C00085
	| SMILES = O=P(O)(O)OC1O(O)(CO)(O)1O		| SMILES = O=P(O)(O)OC1O(O)(CO)(O)1O
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 392657		| ChemSpiderID = 392657
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 16084
	| InChIKey = BGWGXPAPYGQALX-ZXXMMSQZBI		| InChIKey = BGWGXPAPYGQALX-ZXXMMSQZBI
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 643-13-0		| CASNo = 643-13-0
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 2012QM764Y
	| 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		| 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
	}}		}}
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	| pKb =		| pKb =
	| IsoelectricPt =		| IsoelectricPt =
		⚫	}}
	| DeltaHf =
	| DeltaHc =
	}}
	}}		}}
	'''Fructose 6-phosphate''' (also known as the '''Neuberg ester''') is ] sugar ] on carbon 6 (i.e., is a ]). The β-<small>D</small>-form of this compound is very common in ]. The vast majority of ] and fructose entering a cell will become converted to this at some point. The name ''Neuberg ester'' comes from the German biochemist ].		'''Fructose 6-phosphate''' (sometimes called the '''Neuberg ester''') is a derivative of ], which has been ] at the 6-hydroxy group. It is one of several possible ]s. The β-<small>D</small>-form of this compound is very common in ].<ref>{{cite book |last=Berg |first=Jeremy M. |author2=Tymoczko, Stryer |title=Biochemistry |year=2002 |edition=5th |publisher=] |location=New York |isbn=0-7167-3051-0 |url=https://archive.org/details/biochemistrychap00jere |url-access=registration }}</ref><ref>Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. {{ISBN|1-57259-153-6}}.</ref> The great majority of ] is converted to fructose 6-phosphate upon entering a cell. ] is predominantly converted to ] by ] following cellular import.
	==History==		==History==
	In 1918, ] found that the compound (only later identified as fructose 6-phosphate) could be produced by mild acid hydrolysis of "Harden-Young ester" (]).<ref>Fruton, Joseph S. ''Proteins, Enzymes, Genes: The Interplay of Chemistry and Biology''. Yale University Press: New Haven, 1999. p 292</ref>		The name ''Neuberg ester'' comes from the German biochemist ]. In 1918, he found that the compound (later identified as fructose 6-phosphate) was produced by mild acid hydrolysis of ].<ref>Fruton, Joseph S. ''Proteins, Enzymes, Genes: The Interplay of Chemistry and Biology''. Yale University Press: New Haven, 1999. p 292</ref>
	==Fructose 6-phosphate in glycolysis==		==In glycolysis==
	Fructose 6-phosphate lies within the ] ] and is produced by isomerisation of ]. It is in turn further phosphorylated to ].		Fructose 6-phosphate lies within the ] ] and is produced by isomerisation of ]. It is in turn further phosphorylated to ].
			{| style="background: white; text-align:center;"
	{{-}}
			|-
	{{Biochemical Reaction
	|reaction_A_major_substrate=α-<small>D</small>-]		| style="background:lightgreen" | α-{{small|D}}-]
			| colspan="2" style="background:pink; width:75px" | ]
⚫	|reaction_A_major_substrate_image=alpha-D-glucose-6-phosphate_wpmp.png
			| style="background:lightgreen" | α-{{small|D}}-fructose 6-phosphate
	|reaction_A_foward_enzyme=]
			| colspan="2" style="background:pink; width:75px" | ]
	|reaction_A_reverse_enzyme=]
			| style="background:lightgreen" | α-{{small|D}}-]
	|reaction_A_reaction_direction_(foward/reversible/reverse)=reversible
			|-
	|reaction_A_minor_reverse_product(s)=
		⚫	| rowspan="5" | ]
	|reaction_A_minor_reverse_substrate(s)=
			| colspan="2" style="width:75px" | &nbsp;
	|reaction_A_minor_foward_substrate(s)=
			| rowspan="5" | ]
	|reaction_A_minor_foward_product(s)=
			| colspan="2" style="width:75px" | &nbsp;
	|reaction_A_major_product=β-<small>D</small>-fructose 6-phosphate
	|reaction_A_major_product_image=beta-D-fructose-6-phosphate_wpmp.png		| rowspan="5" | ]
			|-
	|reaction_B_foward_enzyme=]
			|
	|reaction_B_reverse_enzyme=]
			|
	|reaction_B_reaction_direction_(foward/reversible/reverse)=reversible
	|reaction_B_minor_foward_substrate(s)=]		| ]
	|reaction_B_minor_foward_product(s)=]		| ]
			|-
	|reaction_B_minor_reverse_product(s)=P<sub>i</sub>
			| colspan="2" style="width:75px" | ]
	|reaction_B_minor_reverse_substrate(s)=H<sub>2</sub>O
			| colspan="2" style="width:75px" | ]
	|reaction_B_major_product=β-<small>D</small>-]
			|-
	|reaction_B_major_product_image=beta-D-fructose-1,6-bisphosphate_wpmp.png
			|
⚫	}}
			|
			| P<sub>i</sub>
			| H<sub>2</sub>O
			|-
			| colspan="2" style="width:75px" | &nbsp;
			| colspan="2" style="width:75px" | &nbsp;
			|-
			| &nbsp;
			| colspan="2" style="background:pink; width:75px" | ]
			| &nbsp;
			| colspan="2" style="background:pink; width:75px" | ]
			| align="right" |
			|}
	{{KEGG compound|C00668}} {{KEGG enzyme|5.3.1.9}} {{KEGG compound|C05345}} {{KEGG enzyme|2.7.1.11}} {{KEGG enzyme|3.1.3.11}} {{KEGG reaction|}} {{KEGG compound|C05378}}		{{KEGG compound|C00668}} {{KEGG enzyme|5.3.1.9}} {{KEGG compound|C05345}} {{KEGG enzyme|2.7.1.11}} {{KEGG enzyme|3.1.3.11}} {{KEGG reaction|}} {{KEGG compound|C05378}}
			{{GlycolysisGluconeogenesis_WP534|highlight=Fructose_6-phosphate}}
	==See also==		==See also==
		⚫	* ]
	* ] is ]. This is one of the regulatory reactions of glycolysis.
⚫	* ] creates ].
	{{Glycolysis}}		{{Glycolysis}}
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	{{reflist}}		{{reflist}}
			{{DEFAULTSORT:Fructosephosphate6}}
			]
	]		]
			]
			]
	{{metabolism-stub}}
			]
	]
	]
⚫	]
	]
	]
	]
	]
	]
	]
	]
	]