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Thiamine pyrophosphate information


Thiamine pyrophosphate
Names
IUPAC name
2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate
Other names
Thiamine diphosphate
Identifiers
CAS Number
  • 136-08-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:9532
ChemSpider
  • 10670483 checkY
KEGG
  • C00068
MeSH Thiamine+pyrophosphate
PubChem CID
  • 1132
UNII
  • Q57971654Y checkY
CompTox Dashboard (EPA)
  • DTXSID2048404 Edit this at Wikidata
InChI
  • InChI=1S/C12H17N4OS.ClH.H4O7P2/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13;;1-8(2,3)7-9(4,5)6/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15);1H;(H2,1,2,3)(H2,4,5,6)/q+1;;/p-1 checkY
    Key: NBSUTVXQOGUTJX-UHFFFAOYSA-M checkY
  • InChI=1/C12H17N4OS.ClH.H4O7P2/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13;;1-8(2,3)7-9(4,5)6/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15);1H;(H2,1,2,3)(H2,4,5,6)/q+1;;/p-1
    Key: NBSUTVXQOGUTJX-REWHXWOFAB
SMILES
  • Cc2ncc(C[n+]1csc(CCOP(=O)(O)OP(=O)(O)O)c1C)c(N)n2
Properties
Chemical formula
C12H19N4O7P2S+
Molar mass 425.314382 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Thiamine pyrophosphate (TPP or ThPP), or thiamine diphosphate (ThDP), or cocarboxylase[1] is a thiamine (vitamin B1) derivative which is produced by the enzyme thiamine diphosphokinase. Thiamine pyrophosphate is a cofactor that is present in all living systems, in which it catalyzes several biochemical reactions.

Thiamine pyrophosphate is synthesized in the cytosol and is required in the cytosol for the activity of transketolase and in the mitochondria for the activity of pyruvate-, oxoglutarate- and branched chain keto acid dehydrogenases. To date, the yeast ThPP carrier (Tpc1p) the human Tpc and the Drosophila melanogaster have been identified as being responsible for the mitochondrial transport of ThPP and ThMP.[2][3][4] It was first discovered as an essential nutrient (vitamin) in humans through its link with the peripheral nervous system disease beriberi, which results from a deficiency of thiamine in the diet.[5]

TPP works as a coenzyme in many enzymatic reactions, such as:

  • Pyruvate dehydrogenase complex[6]
  • Pyruvate decarboxylase in ethanol fermentation
  • Alpha-ketoglutarate dehydrogenase complex
  • Branched-chain amino acid dehydrogenase complex
  • 2-hydroxyphytanoyl-CoA lyase
  • Transketolase
  1. ^ Pietrzak I (1995). "[Vitamin disturbances in chronic renal insufficiency. I. Water soluble vitamins]". Przegla̧d Lekarski (in Polish). 52 (10): 522–5. PMID 8834846.
  2. ^ Marobbio, C. M. T.; Vozza, A.; Harding, M.; Bisaccia, F.; Palmieri, F.; Walker, J. E. (2002-11-01). "Identification and reconstitution of the yeast mitochondrial transporter for thiamine pyrophosphate". The EMBO Journal. 21 (21): 5653–5661. doi:10.1093/emboj/cdf583. ISSN 0261-4189. PMC 131080. PMID 12411483.
  3. ^ Iacopetta, Domenico; Carrisi, Chiara; De Filippis, Giuseppina; Calcagnile, Valeria M.; Cappello, Anna R.; Chimento, Adele; Curcio, Rosita; Santoro, Antonella; Vozza, Angelo (2010-03-01). "The biochemical properties of the mitochondrial thiamine pyrophosphate carrier from Drosophila melanogaster". FEBS Journal. 277 (5): 1172–1181. doi:10.1111/j.1742-4658.2009.07550.x. ISSN 1742-4658. PMID 20121944.
  4. ^ Lindhurst, Marjorie J.; Fiermonte, Giuseppe; Song, Shiwei; Struys, Eduard; Leonardis, Francesco De; Schwartzberg, Pamela L.; Chen, Amy; Castegna, Alessandra; Verhoeven, Nanda (2006-10-24). "Knockout of Slc25a19 causes mitochondrial thiamine pyrophosphate depletion, embryonic lethality, CNS malformations, and anemia". Proceedings of the National Academy of Sciences. 103 (43): 15927–15932. Bibcode:2006PNAS..10315927L. doi:10.1073/pnas.0607661103. ISSN 0027-8424. PMC 1595310. PMID 17035501.
  5. ^ Pavia, Donald L., Gary M. Lampman, George S. Kritz, Randall G. Engel (2006). Introduction to Organic Laboratory Techniques (4th Ed.). Thomson Brooks/Cole. pp. 304–5. ISBN 978-0-495-28069-9.{{cite book}}: CS1 maint: multiple names: authors list (link)
  6. ^ "PDBs for Biochemistry". Georgia State University. Archived from the original on 2011-07-16. Retrieved 2009-02-07.

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Thiamine pyrophosphate

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Thiamine pyrophosphate (TPP or ThPP), or thiamine diphosphate (ThDP), or cocarboxylase is a thiamine (vitamin B1) derivative which is produced by the enzyme...

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Thiamine

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monophosphate (ThMP), thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), adenosine thiamine diphosphate (AThDP) and adenosine thiamine triphosphate (AThTP)...

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Umpolung

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having to rely on the toxic cyanide ion. Thiamine (which itself is an N-heterocyclic carbene) pyrophosphate (TPP) serves a functionally identical role...

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Thiamine deficiency

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Thiamine deficiency is a medical condition of low levels of thiamine (vitamin B1). A severe and chronic form is known as beriberi. The name beriberi is...

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Pyrophosphate

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Phosphoric acids and phosphates RNA Sodium pyrophosphate Superphosphate Thiamine pyrophosphate Tooth Zinc pyrophosphate Yadav, Prerna; Blacque, Olivier; Roodt...

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Oxidative decarboxylation

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acetyltransferase (E2), dihydrolipoamide dehydrogenase (E3), six cofactors: thiamine pyrophosphate (TPP), lipoamide, coenzyme A (CoA), flavin adenine dinucleotide...

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Pyruvate dehydrogenase

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dihydrolipoamide and carbon dioxide. The conversion requires the coenzyme thiamine pyrophosphate. Pyruvate dehydrogenase is usually encountered as a component, referred...

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Enzyme

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flavin mononucleotide (FMN), flavin adenine dinucleotide (FAD), thiamine pyrophosphate (TPP), and tetrahydrofolate (THF), are derived from vitamins. These...

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Thiamine transporter

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structure element through which thiamine pyrophosphate (TPP) levels can regulate transcription of many genes related to thiamine transport, salvage, and de...

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Mitochondrial thiamine pyrophosphate carrier

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Mitochondrial thiamine pyrophosphate carrier is a protein that in humans is encoded by the SLC25A19 gene. Solute carrier family GRCh38: Ensembl release...

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B vitamins

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vitamins are referred to by B-number or by chemical name, such as B1 for thiamine, B2 for riboflavin, and B3 for niacin, while some are more commonly recognized...

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Alcoholic polyneuropathy

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interferes with intestinal absorption of thiamine, thereby further decreasing thiamine levels in the body. Thiamine is important in three reactions in the...

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TPP riboswitch

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conserved RNA secondary structure. It serves as a riboswitch that binds thiamine pyrophosphate (TPP) directly and modulates gene expression through a variety of...

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Prosthetic group

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examples of organic prosthetic groups are vitamin derivatives: thiamine pyrophosphate, pyridoxal-phosphate and biotin. Since prosthetic groups are often...

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Pyruvate decarboxylase

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and carbon dioxide. Pyruvate decarboxylase depends on cofactors thiamine pyrophosphate (TPP) and magnesium. This enzyme should not be mistaken for the...

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Pyruvate dehydrogenase complex

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the binding of two identical E3 monomers. Initially, pyruvate and thiamine pyrophosphate (TPP or vitamin B1) are bound by pyruvate dehydrogenase subunits...

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Thiamine monophosphate

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synthesized by thiamine-phosphate pyrophosphorylase, which combines thiazole in its monophosphate form and pyrimidine as a pyrophosphate. The physiological...

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Anaerobic glycolysis

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acetaldehyde by enzyme pyruvate decarboxylase in the presence of Thiamine pyrophosphate and Mg++. Carbon-dioxide is released during this reaction. Acetaldehyde...

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Vitamin

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all-trans-beta-carotene and other provitamin A carotenoids) Vitamin B1 (thiamine) Vitamin B2 (riboflavin) Vitamin B3 (niacin) Vitamin B5 (pantothenic acid)...

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Clavulanic acid

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glyceraldehyde-3-phosphate with L-arginine in the presence of thiamine diphosphate (TDP or thiamine pyrophosphate), which is the first step of the clavulanic acid...

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Vitamin B1 analogues

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Octotiamine Prosultiamine Sulbutiamine Vintiamol B vitamins Thiamine pyrophosphate, a thiamine derivative Martindale, William (1993). The Extra Pharmacopoeia...

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Thiamine triphosphate

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to thiamine pyrophosphate (ThDP) by a specific thiamine-triphosphatase. It can also be converted into ThDP by thiamine-diphosphate kinase. Thiamine triphosphate...

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Citric acid cycle

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α-Ketoglutarate + NAD+ + CoA-SH α-Ketoglutarate dehydrogenase, Thiamine pyrophosphate, Lipoic acid, Mg++,transsuccinytase Succinyl-CoA + NADH + H + +...

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TDP

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converting biomass into oil Thymidine diphosphate, a nucleotide Thiamine pyrophosphate (thiamine diphosphate), an enzyme cofactor Torsades de pointes, a form...

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Transketolase

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acceleration of enzyme activity after the addition of thiamine pyrophosphate may be diagnostic of thiamine deficiency (0-15% normal, 15-25% deficiency, >25%...

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TPP

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Tripolyphosphate, a sodium salt of the polyphosphate penta-anion Thiamine pyrophosphate, an enzyme cofactor Tetraphenylporphyrin, a synthetic heterocyclic...

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