ジヒドロキシアセトンリン酸 dihydroxyacetone phosphate

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/09/08 15:51:44」(JST)

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Dihydroxyacetone phosphate (DHAP, also glycerone phosphate in older texts) is a biochemical compound involved in many metabolic pathways, including the Calvin cycle in plants and glycolysis.

Role in glycolysis[edit source | edit]

Dihydroxyacetone phosphate lies in the glycolysis metabolic pathway, and is one of the two products of breakdown of fructose 1,6-bisphosphate, along with glyceraldehyde 3-phosphate. It is rapidly and reversibly isomerised to glyceraldehyde 3-phosphate.

β-D-fructose 1,6-bisphosphate	fructose-bisphosphate aldolase	D-glyceraldehyde 3-phosphate		dihydroxyacetone phosphate
			+

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.

Dihydroxyacetone phosphate	triose phosphate isomerase	D-glyceraldehyde 3-phosphate

Compound C00111 at KEGG Pathway Database.Enzyme 5.3.1.1 at KEGG Pathway Database.Compound C00118 at KEGG Pathway Database.

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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Glycolysis and Gluconeogenesis edit

^ The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

Role in other pathways[edit source | edit]

In the Calvin cycle, DHAP is one of the products of the sixfold reduction of 1,3-bisphosphoglycerate by NADPH. It is also used in the synthesis of sedoheptulose 1,7-bisphosphate and fructose 1,6-bisphosphate, both of which are used to reform ribulose 5-phosphate, the 'key' carbohydrate of the Calvin cycle.

DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate, which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD⁺/NADH as cofactor.

DHAP also has a role in the ether-lipid biosynthesis process in the protozoan parasite Leishmania mexicana.

UpToDate Contents

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1. 再発性または難治性のびまん性大細胞型B細胞リンパ腫の治療 treatment of relapsed or refractory diffuse large b cell lymphoma
2. 再発または難治性古典的ホジキンリンパ腫に対するセカンドラインおよびサードライン化学療法レジメンおよび生物学的療法 second and third line chemotherapy regimens and biologic therapy for relapsing or resistant classical hodgkin lymphoma
3. 再発性または難治性の末梢性T細胞リンパ腫の治療 treatment of relapsed or refractory peripheral t cell lymphoma
4. マントル細胞リンパ腫の初期治療 initial treatment of mantle cell lymphoma
5. 再発性または難治性のマントル細胞リンパ腫の治療 treatment of relapsed or refractory mantle cell lymphoma

English Journal

Peripheral T-cell lymphoma: The role of hematopoietic stem cell transplantation.

Gkotzamanidou M1, Papadimitriou CA2.Author information 1Department of Medical Oncology Dana-Farber Cancer Institute, Harvard Medical School, Boston, MA 02115, USA; VA Boston Healthcare System, Harvard Medical School, Boston, MA 02115, USA. Electronic address: maria_gkotzamanidou@dfci.harvard.edu.2Department of Clinical Therapeutics, Alexandra Hospital, Medical School-University of Athens, Greece.AbstractPeripheral T-cell lymphoma (PTCL) is a rare and heterogeneous group of non-Hodgkin lymphomas (NHLs). Whereas the incidence of the disease appears to increase during last decades and the prognosis remains dramatically poor, so far no standard treatment has been established. High-dose chemotherapy and autologous stem cell transplantation (HDT-ASCT) has been proven effective in relapsed PTCL, while retrospective studies have shown a survival benefit as first-line treatment in some subsets of PTCL patients. However, given disease rarity, there is a paucity of randomized trials in both upfront and relapse setting. Here, we critically evaluated eligible prospective and retrospective studies that address the role of ASCT in treatment of PTCL, with respect to quality of design and performance. Additionally, the role of allogeneic transplantation has been reviewed. The comparison of ASCT with novel agents that emerge or the combination of both, are to be ascertained via prospective randomized trials in this field.
Critical reviews in oncology/hematology.Crit Rev Oncol Hematol.2014 Feb;89(2):248-61. doi: 10.1016/j.critrevonc.2013.08.016. Epub 2013 Sep 8.
Peripheral T-cell lymphoma (PTCL) is a rare and heterogeneous group of non-Hodgkin lymphomas (NHLs). Whereas the incidence of the disease appears to increase during last decades and the prognosis remains dramatically poor, so far no standard treatment has been established. High-dose chemotherapy and
PMID 24075060

Sulphoglycolysis in Escherichia coli K-12 closes a gap in the biogeochemical sulphur cycle.

Denger K1, Weiss M2, Felux AK2, Schneider A3, Mayer C3, Spiteller D1, Huhn T4, Cook AM1, Schleheck D1.Author information 1Department of Biology, University of Konstanz, D-78457 Konstanz, Germany.2Konstanz Research School Chemical Biology, University of Konstanz, D-78457 Konstanz, Germany.3Interfaculty Institute of Microbiology and Infection Medicine, University of Tübingen, D-72076 Tübingen, Germany.4Department of Chemistry, University of Konstanz, D-78457 Konstanz, Germany.AbstractSulphoquinovose (SQ, 6-deoxy-6-sulphoglucose) has been known for 50 years as the polar headgroup of the plant sulpholipid in the photosynthetic membranes of all higher plants, mosses, ferns, algae and most photosynthetic bacteria. It is also found in some non-photosynthetic bacteria, and SQ is part of the surface layer of some Archaea. The estimated annual production of SQ is 10,000,000,000 tonnes (10 petagrams), thus it comprises a major portion of the organo-sulphur in nature, where SQ is degraded by bacteria. However, despite evidence for at least three different degradative pathways in bacteria, no enzymic reaction or gene in any pathway has been defined, although a sulphoglycolytic pathway has been proposed. Here we show that Escherichia coli K-12, the most widely studied prokaryotic model organism, performs sulphoglycolysis, in addition to standard glycolysis. SQ is catabolised through four newly discovered reactions that we established using purified, heterologously expressed enzymes: SQ isomerase, 6-deoxy-6-sulphofructose (SF) kinase, 6-deoxy-6-sulphofructose-1-phosphate (SFP) aldolase, and 3-sulpholactaldehyde (SLA) reductase. The enzymes are encoded in a ten-gene cluster, which probably also encodes regulation, transport and degradation of the whole sulpholipid; the gene cluster is present in almost all (>91%) available E. coli genomes, and is widespread in Enterobacteriaceae. The pathway yields dihydroxyacetone phosphate (DHAP), which powers energy conservation and growth of E. coli, and the sulphonate product 2,3-dihydroxypropane-1-sulphonate (DHPS), which is excreted. DHPS is mineralized by other bacteria, thus closing the sulphur cycle within a bacterial community.
Nature.Nature.2014 Jan 26. doi: 10.1038/nature12947. [Epub ahead of print]
Sulphoquinovose (SQ, 6-deoxy-6-sulphoglucose) has been known for 50 years as the polar headgroup of the plant sulpholipid in the photosynthetic membranes of all higher plants, mosses, ferns, algae and most photosynthetic bacteria. It is also found in some non-photosynthetic bacteria, and SQ is part
PMID 24463506

Metabolic flux analysis of recombinant Pichia pastoris growing on different glycerol/methanol mixtures by iterative fitting of NMR-derived (13)C-labelling data from proteinogenic amino acids.

Jordà J, de Jesus SS, Peltier S, Ferrer P, Albiol J.Author information Departament d'Enginyeria Química, Escola d'Enginyeria, Universitat Autònoma de Barcelona, Bellaterra (Cerdanyola del Vallès), Spain.AbstractThe yeast Pichia pastoris has emerged as one of the most promising yeast cell factories for the production of heterologous proteins. The readily available genetic tools and the ease of high-cell density cultivations using methanol or glycerol/methanol mixtures are among the key factors for this development. Previous studies have shown that the use of mixed feeds of glycerol and methanol seem to alleviate the metabolic burden derived from protein production, allowing for higher specific and volumetric process productivities. However, initial studies of glycerol/methanol co-metabolism in P. pastoris by classical metabolic flux analyses using (13)C-derived Metabolic Flux Ratio (METAFoR) constraints were hampered by the reduced labelling information obtained when using C3:C1 substrate mixtures in relation to the conventional C6 substrate, that is, glucose. In this study, carbon flux distributions through the central metabolic pathways in glycerol/methanol co-assimilation conditions have been further characterised using biosynthetically directed fractional (13)C labelling. In particular, metabolic flux distributions were obtained under 3 different glycerol/methanol ratios and growth rates by iterative fitting of NMR-derived (13)C-labelling data from proteinogenic amino acids using the software tool (13)CFlux2. Specifically, cells were grown aerobically in chemostat cultures fed with 80:20, 60:40 and 40:60 (w:w) glycerol/methanol mixtures at two dilutions rates (0.05 hour(-1) and 0.16 hour(-1)), allowing to obtain additional data (biomass composition and extracellular fluxes) to complement pre-existing datasets. The performed (13)C-MFA reveals a significant redistribution of carbon fluxes in the central carbon metabolism as a result of the shift in the dilution rate, while the ratio of carbon sources has a lower impact on carbon flux distribution in cells growing at the same dilution rate. At low growth rate, the percentage of methanol directly dissimilated to CO2 ranges between 50% and 70%. At high growth rate the methanol is completely dissimilated to CO2 by the direct pathway, in the two conditions of highest methanol content.
New biotechnology.N Biotechnol.2014 Jan 25;31(1):120-32. doi: 10.1016/j.nbt.2013.06.007. Epub 2013 Jul 8.
The yeast Pichia pastoris has emerged as one of the most promising yeast cell factories for the production of heterologous proteins. The readily available genetic tools and the ease of high-cell density cultivations using methanol or glycerol/methanol mixtures are among the key factors for this deve
PMID 23845285

Japanese Journal

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
… 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. … We solved the crystal structures of FBPA/P in complex with DHAP (its aldolase form) and FBP (its phosphatase form). …
NAID 130002142893

Molecular and Catalytic Properties of 2,4′-Dihydroxyacetophenone Dioxygenase from Burkholderia sp. AZ11

ENYA Mayu,AOYAGI Keiko,HISHIKAWA Yoshihiro,YOSHIMURA Azusa,MITSUKURA Koichi,MARUYAMA Kiyofumi
Bioscience, Biotechnology, and Biochemistry 76(3), 567-574, 2012
… encoding 2,4′-dihydroxyacetophenone (DHAP) dioxygenase was cloned from Burkholderia … On anaerobic incubation of it with DHAP, the absorption at around 400 nm increased due to the formation of an enzyme-DHAP complex. … for DHAP and the apparent Vmax …
NAID 130001862851

GPD1L Mutations and SCN5A Phosphorylation in Brugada Syndrome

C. Makielski Jonathan
Journal of Arrhythmia 27(Supplement), SY15_3-SY15_3, 2011
… GPD1 catalyzes the reversible conversion of glycerol-3-phosphate (G3P) to dihydroxyacetone phosphate (DHAP). … We hypothesized that like its namesake GPD1, GPD1L catalyzed the reaction of G3P to DHAP. … The G3P to DHAP conversion also causes reduction of NAD+ to NADH, and loss of GPD1L function may also increase reactive oxygen species producing additional effects on SCN5A and other ion channels. …
NAID 130002129793

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★リンクテーブル★

リンク元	「ジヒドロキシアセトンリン酸」「dihydroxyacetone phosphate」
関連記事	「DHA」「DH」

「ジヒドロキシアセトンリン酸」

Dihydroxyacetone phosphate
	IUPAC name 3-Hydroxy-2-oxopropyl phosphate
	Other names Dihydroxyacetone phosphate; DHAP
Identifiers
CAS number	57-04-5
PubChem	4643300
ChemSpider	3833110
ChEBI	CHEBI:57642
Jmol-3D images	Image 1
	SMILES [O-]P([O-])(=O)OCC(=O)CO ;
	InChI InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)/p-2 ; Key: GNGACRATGGDKBX-UHFFFAOYSA-L InChI=1/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)/p-2; Key: GNGACRATGGDKBX-NUQVWONBAJ ;
Properties
Molecular formula	C3H7O6P
Molar mass	170.06 g/mol
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: dihydroxyacetone phosphate, DHAP
関

fructose-1,6-bisphosphate－(aldolase)→glyceraldehyde 3-phosphate + dihydroxyacetone phosphate

CH2-OH
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C=0
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CH2-O-H2PO4

「dihydroxyacetone phosphate」

　　[★] ジヒドロキシアセトンリン酸 DHAP

「DHA」

　　[★]

ドコサヘキサエン酸 docosahexaenoate docosahexaenoic acid
デヒドロエピアンドロステロン dehydoroepiandrosterone
デヒドロ酢酸 dehydroacetic acid

「DH」

　　[★] ドイツ水平線 Deutsche Horizontale

[WikiPathways-1] The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

匿名

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案内

案内

DHAP