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Revision as of 15:45, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,045 edits Saving copy of the {{chembox}} taken from revid 472757558 of page 1,3-Bisphosphoglyceric_acid for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 06:27, 2 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits Fixes image in dark mode 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
|Verifiedfields = changed
| verifiedrevid = 431962359
|verifiedrevid = 477199354
| Name= Bisphosphoglyceric acid
|Name= Bisphosphoglyceric acid
| ImageFile = 1,3-bisphosphoglycerate.png
|ImageFile = 1,3-Bisphosphoglyceric acid.svg
| IUPACName=(2-Hydroxy-3-phosphonooxy-propanoyloxy)phosphonic acid
|ImageClass = skin-invert
| OtherNames =1,3-Diphosphoglycerate; Glycerate-1,3-bisphosphate; Glycerate-1,3-biphosphate; 1,3-Biphosphoglycerate; 3-Phosphoglyceroyl phosphate; Glyceric acid-1,3-diphosphate
|ImageSize = 220
| Section1 = {{Chembox Identifiers
|ImageFile1 = 1,3-Bisphosphoglyceric-acid-3D-balls.png
| Abbreviations=1,3BPG; 1,3-BPG; PGAP
| PubChem = 683 |ImageSize1 = 220
|ImageAlt1 = 1,3-Bisphosphoglyceric acid molecule
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|IUPACName=(2-Hydroxy-3-phosphonooxy-propanoyloxy)phosphonic acid
| ChemSpiderID = 663
|OtherNames =1,3-Diphosphoglycerate; Glycerate-1,3-bisphosphate; Glycerate-1,3-biphosphate; 1,3-Biphosphoglycerate; 3-Phosphoglyceroyl phosphate; Glyceric acid-1,3-diphosphate
| InChI = 1/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)
|Section1 = {{Chembox Identifiers
| InChIKey = LJQLQCAXBUHEAZ-UHFFFAOYAI
|Abbreviations=1,3BPG; 1,3-BPG; PGAP
| SMILES = O=C(OP(=O)(O)O)C(O)COP(=O)(O)O
|PubChem = 683
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| StdInChI = 1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)
|ChemSpiderID = 663
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|InChI = 1/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)
| StdInChIKey = LJQLQCAXBUHEAZ-UHFFFAOYSA-N
|InChIKey = LJQLQCAXBUHEAZ-UHFFFAOYAI
| CASNo_Ref = {{cascite|correct|??}}
|SMILES = O=C(OP(=O)(O)O)C(O)COP(=O)(O)O
| CASNo = <!-- blanked - oldvalue: 1981-49-3 -->
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = LJQLQCAXBUHEAZ-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|changed|??}}
|CASNo = 1981-49-3
}} }}
| Section2 = {{Chembox Properties |Section2 = {{Chembox Properties
| C=3|H=8|O=10|P=2 |C=3|H=8|O=10|P=2
| Density =
| MeltingPt =
| BoilingPt =
}}
}} }}
}}

'''1,3-Bisphosphoglyceric acid''' ('''1,3-Bisphosphoglycerate''' or '''1,3BPG''') is a 3-carbon organic molecule present in most, if not all, living organisms. It primarily exists as a metabolic intermediate in both ] during ] and the ] during ]. 1,3BPG is a transitional stage between ] and ] during the fixation/reduction of ]. 1,3BPG is also a precursor to ] which in turn is a reaction intermediate in the glycolytic pathway.

==Biological structure and role==
1,3-Bisphosphoglycerate is the ] of 1,3-bisphosphoglyceric acid. It is phosphorylated at the number 1 and 3 carbons. The result of this phosphorylation gives 1,3BPG important biological properties such as the ability to phosphorylate ] to form the energy storage molecule ATP.

===In glycolysis===
<div style="border:1px #aaa solid; overflow:auto">
{| style="background: white; text-align:center;"
|-
| style="background:lightgreen" | {{small|D}}-]
| colspan="2" style="background:pink; width:75px" | ]
| style="background:lightgreen" | ]
| colspan="2" style="background:pink; width:75px" | ]
| style="background:lightgreen" | ]
|-
| rowspan="5" | ]
| colspan="2" style="width:75px" | &nbsp;
| rowspan="5" | ]
| colspan="2" style="width:75px" | &nbsp;
| rowspan="5" | ]
|- style="vertical-align: bottom;"
| NAD<sup>+</sup><br>'''+'''<br>P<sub>i</sub>
| NADH<br>'''+'''<br>H<sup>+</sup>
| ]
| ]
|-
| colspan="2" style="width:75px" | ]
| colspan="2" style="width:75px" | ]
|- style="vertical-align: top;"
| NAD<sup>+</sup><br>'''+'''<br>P<sub>i</sub>
| NADH<br>'''+'''<br>H<sup>+</sup>
| ]
| ]
|-
| 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" |
|}
</div>
{{KEGG compound|C00118}} {{KEGG enzyme|1.2.1.12}} {{KEGG compound|C00236}} {{KEGG enzyme|2.7.2.3}} {{KEGG compound|C00197}}

As previously mentioned 1,3BPG is a metabolic intermediate in the ]. It is created by the ] ] of the ] in ]. The result of this oxidation is the conversion of the aldehyde group into a ] group which drives the formation of an acyl phosphate bond. This is incidentally the only step in the glycolytic pathway in which ] is converted into ]. The formation reaction of 1,3BPG requires the presence of an enzyme called ].

The ] bond of 1,3BPG is important in ] as it assists in the formation of ]. The molecule of ATP created during the following reaction is the first molecule produced during respiration. The reaction occurs as follows;

:1,3-bisphosphoglycerate + ADP ⇌ 3-phosphoglycerate + ATP

The transfer of an ] from the carboxyl group on 1,3BPG to ADP to form ATP is reversible due to a low ]. This is as a result of one acyl phosphate bond being cleaved whilst another is created. This reaction is not naturally spontaneous and requires the presence of a ]. This role is performed by the ] ]. During the reaction phosphoglycerate kinase undergoes a substrate induced conformational change similar to another metabolic enzyme called ].

Because two molecules of glyceraldehyde-3-phosphate are formed during glycolysis from one molecule of glucose, 1,3BPG can be said to be responsible for two of the ten molecules of ATP produced during the entire process. Glycolysis also uses two molecules of ATP in its initial stages as a ]. For this reason glycolysis is not reversible and has a net produce of 2 molecules of ATP and two of NADH. The two molecules of NADH themselves go on to produce approximately 3 molecules of ATP each.

{{GlycolysisGluconeogenesis_WP534|highlight=1,3-Bisphosphoglyceric_acid}}

===In the Calvin cycle===
1,3-BPG has a very similar role in the ] to its role in the glycolytic pathway. For this reason both reactions are said to be analogous. However the reaction pathway is effectively reversed. The only other major difference between the two reactions is that NADPH is used as an electron donor in the calvin cycle whilst NAD<sup>+</sup> is used as an electron acceptor in glycolysis. In this reaction cycle 1,3BPG originates from ] and is made into ] by the action of specific enzymes.

Contrary to the similar reactions of the glycolytic pathway, 1,3BPG in the Calvin cycle does not produce ATP but instead uses it. For this reason it can be considered to be an irreversible and committed step in the cycle. The outcome of this section of the cycle is an inorganic phosphate is removed from 1,3BPG as a hydrogen ion and two electrons are added to the compound<sup>+</sup>.

In complete reverse of the glycolytic pathway reaction, the enzyme phosphoglycerate kinase catalyses the reduction of the ] group of 1,3BPG to form an ] instead. This reaction also releases an ] molecule which is subsequently used as energy for the donation of electrons from the conversion of NADPH to NADP<sup>+</sup>. Overseeing this latter stage of the reaction is the enzyme glyceraldehyde-phosphate dehydrogenase.

===In oxygen transfer===
During normal ] in humans approximately 20% of the 1,3BPG produced does not go any further in the glycolytic pathway. It is instead shunted through an alternate pathway involving the reduction of ATP in the ]. During this alternate pathway it is made into a similar molecule called ] (2,3BPG). 2,3BPG is used as a mechanism to oversee the efficient release of ] from ]. Levels of this 1,3BPG will raise in a patient's blood when oxygen levels are low as this is one of the mechanisms of ]. Low oxygen levels trigger a rise in 1,3BPG levels which in turn raises the level of 2,3BPG which alters the efficiency of oxygen dissociation from hemoglobin.

==References==
{{Reflist}}

*{{cite book |title=Molecular Biology of the Cell |last=Alberts |first=Bruce |year=2001 |publisher=Garland Science |location=New York |isbn=0-8153-4072-9 |display-authors=etal}}
*{{cite book |title=Principles of Human Physiology |last=Germann |first=William J. |author2=Stanfield, Cindy L. |year=2002 |publisher=Benjamin Cummings |location=San Francisco |isbn=0-8053-6056-5 |url=https://archive.org/details/principlesofhuma0000germ |url-access=registration }}
*{{cite book |title=Biochemistry |last=Stryer |first=Lubert |year=2002 |edition=5th |publisher=W. H. Freeman |location=New York |isbn=0-7167-4684-0 |url=https://archive.org/details/biochemistry200100jere|url-access=registration |display-authors=etal}}

==External links==
*
*
* {{Webarchive|url=https://archive.today/20130414173856/http://content.febsjournal.org/cgi/content/abstract/186/1/265 |date=2013-04-14 }}

{{Glycolysis}}

{{Authority control}}

{{DEFAULTSORT:Bisphosphoglyceric Acid, 1, 3-}}
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