同: BPG

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/13 22:25:04」(JST)

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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 glycolysis during respiration and the Calvin cycle during photosynthesis. 1,3BPG is a transitional stage between glycerate 3-phosphate and glyceraldehyde 3-phosphate during the fixation/reduction of CO₂. 1,3BPG is also a precursor to 2,3-bisphosphoglycerate which in turn is a reaction intermediate in the glycolytic pathway.

Biological structure and role

1,3-Bisphosphoglycerate is the conjugate base 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 ADP to form the energy storage molecule ATP.

In glycolysis

D-glyceraldehyde 3-phosphate	glyceraldehyde phosphate dehydrogenase		1,3-bisphospho-D-glycerate	3-phosphoglycerate kinase		3-phospho-D-glycerate

	NAD⁺ + P_i	NADH + H⁺		ADP	ATP

	NAD⁺ + P_i	NADH + H⁺		ADP	ATP

	glyceraldehyde phosphate dehydrogenase			3-phosphoglycerate kinase

Compound C00118 at KEGG Pathway Database. Enzyme 1.2.1.12 at KEGG Pathway Database. Compound C00236 at KEGG Pathway Database. Enzyme 2.7.2.3 at KEGG Pathway Database. Compound C00197 at KEGG Pathway Database.

As previously mentioned 1,3BPG is a metabolic intermediate in the glycolytic pathway. It is created by the exergonic oxidation of the aldehyde in G3P. The result of this oxidation is the conversion of the aldehyde group into a carboxylic acid group which drives the formation of an acyl phosphate bond. This is incidentally the only step in the glycolytic pathway in which NAD⁺ is converted into NADH. The formation reaction of 1,3BPG requires the presence of an enzyme called glyceraldehyde-3-phosphate dehydrogenase.

The high-energy acyl phosphate bond of 1,3BPG is important in respiration as it assists in the formation of ATP. 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 inorganic phosphate from the carboxyl group on 1,3BPG to ADP to form ATP is reversible due to a low ΔG. 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 catalyst. This role is performed by the enzyme phosphoglycerate kinase. During the reaction phosphoglycerate kinase undergoes a substrate induced conformational change similar to another metabolic enzyme called hexokinase.

Because two molecules of glyceraldehyde-3-phosphate are formed during glycolysis from one molecule of glucose, 1,3BPG can be said to 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 committed and irreversible step. 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.

In the calvin cycle

1,3-BPG has a very similar role in the Calvin cycle 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⁺ is used as an electron acceptor in glycolysis. In this reaction cycle 1,3BPG originates from 3-phosphoglycerate and is made into glyceraldehyde 3-phosphate 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⁺.

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

In oxygen transfer

During normal metabolism 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 erythrocytes. During this alternate pathway it is made into a similar molecule called 2,3-bisphosphoglyceric acid (2,3BPG). 2,3BPG is used as a mechanism to oversee the efficient release of oxygen from hemoglobin. Levels of this 1,3BPG will raise in a patients blood when oxygen levels are low as this is one of the mechanisms of acclimatization. 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

Alberts, Bruce; et al. (2001). Molecular Biology of the Cell. New York: Garland Science. ISBN 0-8153-4072-9.
Germann, William J.; Stanfield, Cindy L. (2002). Principles of Human Physiology. San Francisco: Benjamin Cummings. ISBN 0-8053-6056-5.
Stryer, Lubert; et al. (2002). Biochemistry (5th ed.). New York: W. H. Freeman. ISBN 0-7167-4684-0.

External links

1,3BPG in Glycolysis and Fermentation
Medical Dictionary reference for 1,3BPG
1,3BPG enzyme mechanisms
1,3BPG in Photosynthesis

UpToDate Contents

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English Journal

CP12-mediated protection of Calvin-Benson cycle enzymes from oxidative stress.

Marri L, Thieulin-Pardo G, Lebrun R, Puppo R, Zaffagnini M, Trost P, Gontero B, Sparla F.SourceDepartment of Pharmacy and Biotechnology, University of Bologna, Via Irnerio 42, 40126 Bologna, Italy.
Biochimie.Biochimie.2013 Nov 5. pii: S0300-9084(13)00389-1. doi: 10.1016/j.biochi.2013.10.018. [Epub ahead of print]
Glyceraldehyde-3-phosphate dehydrogenase (GAPDH) and phosphoribulokinase (PRK) are two energy-consuming enzymes of the Calvin-Benson cycle, whose regulation is crucial for the global balance of the photosynthetic process under different environmental conditions. In oxygen phototrophs, GAPDH and PRK
PMID 24211189

Kinetic and mechanistic characterization of the glyceraldehyde 3-phosphate dehydrogenase from Mycobacterium tuberculosis.

Wolfson-Stofko B, Hadi T, Blanchard JS.SourceDepartment of Biochemistry, Albert Einstein College of Medicine, 1300 Morris Park Avenue, Bronx, NY 10461, United States.
Archives of biochemistry and biophysics.Arch Biochem Biophys.2013 Oct 23;540(1-2):53-61. doi: 10.1016/j.abb.2013.10.007. [Epub ahead of print]
Glyceraldehyde 3-phosphate dehydrogenase (GAPDH) is a glycolytic protein responsible for the conversion of glyceraldehyde 3-phosphate (G3P), inorganic phosphate and nicotinamide adenine dinucleotide (NAD+) to 1,3-bisphosphoglycerate (1,3-BPG) and the reduced form of nicotinamide adenine dinucleotide
PMID 24161676

Improved Production of 2,3-Butanediol in Bacillus amyloliquefaciens by Over-Expression of Glyceraldehyde-3-Phosphate Dehydrogenase and 2,3-butanediol Dehydrogenase.

Yang T, Rao Z, Zhang X, Xu M, Xu Z, Yang ST.SourceThe Key Laboratory of Industrial Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, Jiangsu Province, China.
PloS one.PLoS One.2013 Oct 2;8(10):e76149. doi: 10.1371/journal.pone.0076149.
BACKGROUND: Previously, a safe strain, Bacillus amyloliquefaciens B10-127 was identified as an excellent candidate for industrial-scale microbial fermentation of 2,3-butanediol (2,3-BD). However, B. amyloliquefaciens fermentation yields large quantities of acetoin, lactate and succinate as by-produc
PMID 24098433

Japanese Journal

The bifunctional glyceryl transferase/phosphatase OzmB belonging to the HAD superfamily that diverts 1,3-bisphosphoglycerate into polyketide biosynthesis

J Am Chem Soc 128, 10386-10387, 2006
NAID 30011177602

補酵素NADモデル分子を用いた生体酸化・不斉還元モデル反応

有機合成化学協会誌 57(6), 512-522, 1999-06-01
NAID 10009347966

Regulation of glucose 1,6-bisphosphate level in liver. III. Purification and properties of bovine glucose 1,6-bisphosphate synthase.:III. Purification and Properties of Bovine Glucose 1, 6-Bisphosphate Synthase

The Journal of Biochemistry 83(6), 1721-1730, 1978
NAID 130003540673

Related Pictures

phosphate to 1 3 bisphosphoglycerate bis phosphoglycerate confused with the formation of NADH ATP AND OXIDATIVE PHOSPHORYLATION of adp by 1 3 bisphosphoglycerate Description 1,3-bisphosphoglycerate.png Bisphosphoglycerate (1,3-BPG)

★リンクテーブル★

リンク元	「解糖系」「1,3-ビスホスホグリセリン酸」「1,3-BPG」
関連記事	「bisphosphoglycerate」

「解糖系」

Bisphosphoglyceric acid
	IUPAC name (2-Hydroxy-3-phosphonooxy-propanoyloxy)phosphonic acid
	Other names 1,3-Diphosphoglycerate; Glycerate-1,3-bisphosphate; Glycerate-1,3-biphosphate; 1,3-Biphosphoglycerate; 3-Phosphoglyceroyl phosphate; Glyceric acid-1,3-diphosphate
Identifiers
Abbreviations	1,3BPG; 1,3-BPG; PGAP
CAS number	1981-49-3
PubChem	683
ChemSpider	663
Jmol-3D images	Image 1
	SMILES O=C(OP(=O)(O)O)C(O)COP(=O)(O)O ;
	InChI InChI=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) ; Key: LJQLQCAXBUHEAZ-UHFFFAOYSA-N 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); Key: LJQLQCAXBUHEAZ-UHFFFAOYAI ;
Properties
Molecular formula	C3H8O10P2
Molar mass	266.04 g mol−1
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

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

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