Thiamine pyrophosphate

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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH Thiamine+pyrophosphate
UNII
  • 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
  • Cc2ncc(C[n+]1csc(CCOP(=O)(O)OP(=O)(O)O)c1C)c(N)n2
Properties
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 ?)

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:

  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.