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Wikipedia

Thiamine triphosphate

Thiamine triphosphate (ThTP) is a biomolecule found in most organisms including bacteria, fungi, plants and animals.[1] Chemically, it is the triphosphate derivative of the vitamin thiamine.

Thiamine triphosphate
Identifiers
  • 3475-65-8 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:18284 Y
ChemSpider
  • 17927 Y
MeSH Thiamine+triphosphate
  • 18989
UNII
  • 464M6AQ7IV Y
  • DTXSID80956233
  • InChI=1S/C12H19N4O10P3S/c1-8-11(30-7-16(8)6-10-5-14-9(2)15-12(10)13)3-4-24-28(20,21)26-29(22,23)25-27(17,18)19/h5,7H,3-4,6H2,1-2H3,(H5-,13,14,15,17,18,19,20,21,22,23) Y
    Key: IWLROWZYZPNOFC-UHFFFAOYSA-N Y
  • InChI=1/C12H19N4O10P3S/c1-8-11(30-7-16(8)6-10-5-14-9(2)15-12(10)13)3-4-24-28(20,21)26-29(22,23)25-27(17,18)19/h5,7H,3-4,6H2,1-2H3,(H5-,13,14,15,17,18,19,20,21,22,23)
    Key: IWLROWZYZPNOFC-UHFFFAOYAE
  • Cc1c(sc[n+]1Cc2cnc(nc2N)C)CCOP(=O)(O)OP(=O)(O)OP(=O)(O)[O-]
Properties
C12H19N4O10P3S
Molar mass 504.288
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Function edit

It has been proposed that ThTP has a specific role in nerve excitability,[2] but this has never been confirmed and recent results suggest that ThTP probably plays a role in cell energy metabolism.[1][3] Low or absent levels of thiamine triphosphate have been found in Leighs disease.[4] [5]

In E. coli, ThTP is accumulated in the presence of glucose during amino acid starvation.[1][3] On the other hand, suppression of the carbon source leads to the accumulation, of adenosine thiamine triphosphate (AThTP).

Metabolism edit

It has been shown that in brain ThTP is synthesized in mitochondria by a chemiosmotic mechanism, perhaps similar to ATP synthase.[6] In mammals, ThTP is hydrolyzed to thiamine pyrophosphate (ThDP) by a specific thiamine-triphosphatase.[3][7] It can also be converted into ThDP by thiamine-diphosphate kinase.

History edit

Thiamine triphosphate (ThTP) was chemically synthesized in 1948 at a time when the only organic triphosphate known was ATP.[8] The first claim of the existence of ThTP in living organisms was made in rat liver,[9] followed by baker’s yeast.[10] Its presence was later confirmed in rat tissues[11] and in plants germs, but not in seeds, where thiamine was essentially unphosphorylated.[12] In all those studies, ThTP was separated from other thiamine derivatives using a paper chromatographic method, followed by oxidation in fluorescent thiochrome compounds with ferricyanide in alkaline solution. This method is at best semi-quantitative, and the development of liquid chromatographic methods suggested that ThTP represents far less than 10% of total thiamine in animal tissues.[13]

References edit

  1. ^ a b c Makarchikov AF, Lakaye B, Gulyai IE, Czerniecki J, Coumans B, Wins P, Grisar T, Bettendorff L (2003). "Thiamine triphosphate and thiamine triphosphatase activities: from bacteria to mammals". Cell. Mol. Life Sci. 60 (7): 1477–88. doi:10.1007/s00018-003-3098-4. PMID 12943234. S2CID 25400487.
  2. ^ Matsuda, T; Cooper, JR (1981). "Thiamine as an integral component of brain synaptosomal membranes". Proceedings of the National Academy of Sciences of the United States of America. 78 (9): 5886–9. Bibcode:1981PNAS...78.5886M. doi:10.1073/pnas.78.9.5886. PMC 348897. PMID 6272323.
  3. ^ a b c Lakaye, B.; Makarchikov, AF; Antunes, AF; Zorzi, W; Coumans, B; De Pauw, E; Wins, P; Grisar, T; Bettendorff, L (2002). "Molecular Characterization of a Specific Thiamine Triphosphatase Widely Expressed in Mammalian Tissues". Journal of Biological Chemistry. 277 (16): 13771–7. doi:10.1074/jbc.M111241200. PMID 11827967.
  4. ^ Murphy, J. V.; Craig, L. (1975). "Leigh's disease: Significance of the biochemical changes in brain". Journal of Neurology, Neurosurgery, and Psychiatry. 38 (11): 1100–1103. doi:10.1136/jnnp.38.11.1100. PMC 492163. PMID 1206418.
  5. ^ Murphy, Jerome V. (1974). "Leigh Disease". Archives of Neurology. 31 (4): 220. doi:10.1001/archneur.1974.00490400034002.
  6. ^ Gangolf, M.; Wins, P.; Thiry, M.; El Moualij, B.; Bettendorff, L. (2009). "Thiamine Triphosphate Synthesis in Rat Brain Occurs in Mitochondria and is Coupled to the Respiratory Chain". Journal of Biological Chemistry. 285 (1): 583–94. doi:10.1074/jbc.M109.054379. PMC 2804207. PMID 19906644.
  7. ^ Song, J.; Bettendorff, L.; Tonelli, M.; Markley, J. L. (2008). "Structural Basis for the Catalytic Mechanism of Mammalian 25-kDa Thiamine Triphosphatase". Journal of Biological Chemistry. 283 (16): 10939–48. doi:10.1074/jbc.M709675200. PMC 2447667. PMID 18276586.
  8. ^ Velluz L., Amiard G. & Bartos J. (1948). "Un nouveau derive de phosphorylation de la vitamine=B1, lacide thiamine triphosphorique". J. Bull. Soc. Chim. Fr. 15: 871.
  9. ^ Rossi-Fanelli A., Siliprandi N. & Fasella P. (1952). "On the presence of triphosphothiamine (TPT) in the liver". Science. 116 (3026): 711–713. Bibcode:1952Sci...116..711R. doi:10.1126/science.116.3026.711. PMID 13028255.
  10. ^ Kiessling K.-H. (1953). "Thiamine triphosphate in baker's yeast". Nature. 172 (4391): 1187–1188. Bibcode:1953Natur.172.1187K. doi:10.1038/1721187a0. PMID 13111284. S2CID 4289038.
  11. ^ Greiling H. & Kiesow L. (1958). "Zur Biochemie der Thiamintriphosphorsäure IV. Das Vorkommen von Thiamintriphosphat im tierischen Organismus". Zeitschrift für Naturforschung B. 13: 251–252. doi:10.1515/znb-1958-0412.
  12. ^ Yusa T. (1962). "Studies on thiamine triphosphate II. Thiamine triphosphate as phosphate donor". Plant Cell. 3: 95–103.
  13. ^ Rindi G. & de Giuseppe L. (1961). "A new chromatographic method for the determination of thiamine and its mono-, di- and triphosphates in animal tissues". Biochem. J. 78 (3): 602–606. doi:10.1042/bj0780602. PMC 1205381. PMID 13741738.

thiamine, triphosphate, thtp, biomolecule, found, most, organisms, including, bacteria, fungi, plants, animals, chemically, triphosphate, derivative, vitamin, thiamine, identifierscas, number, 3475, model, jsmol, interactive, imagechebi, chebi, 18284, ychemspi. Thiamine triphosphate ThTP is a biomolecule found in most organisms including bacteria fungi plants and animals 1 Chemically it is the triphosphate derivative of the vitamin thiamine Thiamine triphosphate IdentifiersCAS Number 3475 65 8 Y3D model JSmol Interactive imageChEBI CHEBI 18284 YChemSpider 17927 YMeSH Thiamine triphosphatePubChem CID 18989UNII 464M6AQ7IV YCompTox Dashboard EPA DTXSID80956233InChI InChI 1S C12H19N4O10P3S c1 8 11 30 7 16 8 6 10 5 14 9 2 15 12 10 13 3 4 24 28 20 21 26 29 22 23 25 27 17 18 19 h5 7H 3 4 6H2 1 2H3 H5 13 14 15 17 18 19 20 21 22 23 YKey IWLROWZYZPNOFC UHFFFAOYSA N YInChI 1 C12H19N4O10P3S c1 8 11 30 7 16 8 6 10 5 14 9 2 15 12 10 13 3 4 24 28 20 21 26 29 22 23 25 27 17 18 19 h5 7H 3 4 6H2 1 2H3 H5 13 14 15 17 18 19 20 21 22 23 Key IWLROWZYZPNOFC UHFFFAOYAESMILES Cc1c sc n 1Cc2cnc nc2N C CCOP O O OP O O OP O O O PropertiesChemical formula C12H19N4O10P3SMolar mass 504 288Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Function 2 Metabolism 3 History 4 ReferencesFunction editIt has been proposed that ThTP has a specific role in nerve excitability 2 but this has never been confirmed and recent results suggest that ThTP probably plays a role in cell energy metabolism 1 3 Low or absent levels of thiamine triphosphate have been found in Leighs disease 4 5 In E coli ThTP is accumulated in the presence of glucose during amino acid starvation 1 3 On the other hand suppression of the carbon source leads to the accumulation of adenosine thiamine triphosphate AThTP Metabolism editIt has been shown that in brain ThTP is synthesized in mitochondria by a chemiosmotic mechanism perhaps similar to ATP synthase 6 In mammals ThTP is hydrolyzed to thiamine pyrophosphate ThDP by a specific thiamine triphosphatase 3 7 It can also be converted into ThDP by thiamine diphosphate kinase History editThiamine triphosphate ThTP was chemically synthesized in 1948 at a time when the only organic triphosphate known was ATP 8 The first claim of the existence of ThTP in living organisms was made in rat liver 9 followed by baker s yeast 10 Its presence was later confirmed in rat tissues 11 and in plants germs but not in seeds where thiamine was essentially unphosphorylated 12 In all those studies ThTP was separated from other thiamine derivatives using a paper chromatographic method followed by oxidation in fluorescent thiochrome compounds with ferricyanide in alkaline solution This method is at best semi quantitative and the development of liquid chromatographic methods suggested that ThTP represents far less than 10 of total thiamine in animal tissues 13 References edit a b c Makarchikov AF Lakaye B Gulyai IE Czerniecki J Coumans B Wins P Grisar T Bettendorff L 2003 Thiamine triphosphate and thiamine triphosphatase activities from bacteria to mammals Cell Mol Life Sci 60 7 1477 88 doi 10 1007 s00018 003 3098 4 PMID 12943234 S2CID 25400487 Matsuda T Cooper JR 1981 Thiamine as an integral component of brain synaptosomal membranes Proceedings of the National Academy of Sciences of the United States of America 78 9 5886 9 Bibcode 1981PNAS 78 5886M doi 10 1073 pnas 78 9 5886 PMC 348897 PMID 6272323 a b c Lakaye B Makarchikov AF Antunes AF Zorzi W Coumans B De Pauw E Wins P Grisar T Bettendorff L 2002 Molecular Characterization of a Specific Thiamine Triphosphatase Widely Expressed in Mammalian Tissues Journal of Biological Chemistry 277 16 13771 7 doi 10 1074 jbc M111241200 PMID 11827967 Murphy J V Craig L 1975 Leigh s disease Significance of the biochemical changes in brain Journal of Neurology Neurosurgery and Psychiatry 38 11 1100 1103 doi 10 1136 jnnp 38 11 1100 PMC 492163 PMID 1206418 Murphy Jerome V 1974 Leigh Disease Archives of Neurology 31 4 220 doi 10 1001 archneur 1974 00490400034002 Gangolf M Wins P Thiry M El Moualij B Bettendorff L 2009 Thiamine Triphosphate Synthesis in Rat Brain Occurs in Mitochondria and is Coupled to the Respiratory Chain Journal of Biological Chemistry 285 1 583 94 doi 10 1074 jbc M109 054379 PMC 2804207 PMID 19906644 Song J Bettendorff L Tonelli M Markley J L 2008 Structural Basis for the Catalytic Mechanism of Mammalian 25 kDa Thiamine Triphosphatase Journal of Biological Chemistry 283 16 10939 48 doi 10 1074 jbc M709675200 PMC 2447667 PMID 18276586 Velluz L Amiard G amp Bartos J 1948 Un nouveau derive de phosphorylation de la vitamine B1 lacide thiamine triphosphorique J Bull Soc Chim Fr 15 871 Rossi Fanelli A Siliprandi N amp Fasella P 1952 On the presence of triphosphothiamine TPT in the liver Science 116 3026 711 713 Bibcode 1952Sci 116 711R doi 10 1126 science 116 3026 711 PMID 13028255 Kiessling K H 1953 Thiamine triphosphate in baker s yeast Nature 172 4391 1187 1188 Bibcode 1953Natur 172 1187K doi 10 1038 1721187a0 PMID 13111284 S2CID 4289038 Greiling H amp Kiesow L 1958 Zur Biochemie der Thiamintriphosphorsaure IV Das Vorkommen von Thiamintriphosphat im tierischen Organismus Zeitschrift fur Naturforschung B 13 251 252 doi 10 1515 znb 1958 0412 Yusa T 1962 Studies on thiamine triphosphate II Thiamine triphosphate as phosphate donor Plant Cell 3 95 103 Rindi G amp de Giuseppe L 1961 A new chromatographic method for the determination of thiamine and its mono di and triphosphates in animal tissues Biochem J 78 3 602 606 doi 10 1042 bj0780602 PMC 1205381 PMID 13741738 Retrieved from https en wikipedia org w index php title Thiamine triphosphate amp oldid 1045739406, wikipedia, wiki, book, books, library,

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