| Revision as of 12:56, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 455026483 of page Thiamine_triphosphate for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 14:07, 19 August 2024 edit Teaktl17 (talk | contribs)Extended confirmed users18,074 editsm →Metabolism: +wl |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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| verifiedrevid = 447671939 |
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| verifiedrevid = 470606262 |
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|ImageFile=Thiamintriphosphat.svg |
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| ImageFile=Thiamintriphosphat.svg |
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|IUPACName= |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 17927 |
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| ChemSpiderID = 17927 |
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| 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) |
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| 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) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IWLROWZYZPNOFC-UHFFFAOYSA-N |
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| StdInChIKey = IWLROWZYZPNOFC-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 3475-65-8 --> |
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| CASNo=3475-65-8 |
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| PubChem=18989 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 464M6AQ7IV |
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| PubChem=18989 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 18284 |
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| ChEBI = 18284 |
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| SMILES = Cc1c(sc1Cc2cnc(nc2N)C)CCOP(=O)(O)OP(=O)(O)OP(=O)(O) |
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| SMILES = Cc1c(sc1Cc2cnc(nc2N)C)CCOP(=O)(O)OP(=O)(O)OP(=O)(O) |
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| MeSHName=Thiamine+triphosphate |
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| MeSHName=Thiamine+triphosphate |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>12</sub>H<sub>19</sub>N<sub>4</sub>O<sub>10</sub>P<sub>3</sub>S |
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| Formula=C<sub>12</sub>H<sub>19</sub>N<sub>4</sub>O<sub>10</sub>P<sub>3</sub>S |
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| MolarMass=504.288 |
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| MolarMass=504.288 |
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|Section3= {{Chembox Hazards |
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'''Thiamine triphosphate''' (ThTP) is a biomolecule found in most organisms including ], ], ]s and ]s.<ref name="Ref1">{{cite journal |vauthors = Makarchikov AF, Lakaye B, Gulyai IE, Czerniecki J, Coumans B, Wins P, Grisar T, Bettendorff L |title=Thiamine triphosphate and thiamine triphosphatase activities: from bacteria to mammals |journal=Cell. Mol. Life Sci. |volume=60 |issue=7 |pages=1477–88 |year=2003 |pmid=12943234 |doi=10.1007/s00018-003-3098-4 |s2cid=25400487 |pmc=11146050 }}</ref> Chemically, it is the ] ] of the vitamin ]. |
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==Function== |
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It has been proposed that ThTP has a specific role in nerve excitability,<ref name="Ref2">{{Cite journal | pmid=6272323 | pmc=348897 | year=1981 | last1=Matsuda | first1=T | last2=Cooper | first2=JR | title=Thiamine as an integral component of brain synaptosomal membranes | volume=78 | issue=9 | pages=5886–9 | journal=Proceedings of the National Academy of Sciences of the United States of America | doi=10.1073/pnas.78.9.5886| bibcode=1981PNAS...78.5886M | doi-access=free }}</ref> but this has never been confirmed and recent results suggest that ThTP probably plays a role in cell energy metabolism.<ref name="Ref1" /><ref name="Ref3">{{cite journal | doi = 10.1074/jbc.M111241200 | title = Molecular Characterization of a Specific Thiamine Triphosphatase Widely Expressed in Mammalian Tissues | year = 2002 | last1 = Lakaye | first1 = B. | journal = Journal of Biological Chemistry | volume = 277 | issue = 16 | pages = 13771–7 | pmid = 11827967 | last2 = Makarchikov | first2 = AF | last3 = Antunes | first3 = AF | last4 = Zorzi | first4 = W | last5 = Coumans | first5 = B | last6 = De Pauw | first6 = E | last7 = Wins | first7 = P | last8 = Grisar | first8 = T | last9 = Bettendorff | first9 = L | doi-access = free }}</ref> Low or absent levels of thiamine triphosphate have been found in ].<ref>{{Cite journal | pmc = 492163| year = 1975| last1 = Murphy| first1 = J. V.| title = Leigh's disease: Significance of the biochemical changes in brain| journal = Journal of Neurology, Neurosurgery, and Psychiatry| volume = 38| issue = 11| pages = 1100–1103| last2 = Craig| first2 = L.| pmid = 1206418| doi=10.1136/jnnp.38.11.1100}}</ref> <ref>{{cite journal | doi = 10.1001/archneur.1974.00490400034002 | title = Leigh Disease | journal = Archives of Neurology | volume = 31 | issue = 4 | pages = 220 | year = 1974 | last1 = Murphy | first1 = Jerome V. }}</ref> |
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In '']'', ThTP is accumulated in the presence of ] during ] starvation.<ref name="Ref1" /><ref name="Ref3" /> On the other hand, suppression of the carbon source leads to the accumulation, of ] (AThTP). |
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==Metabolism== |
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It has been shown that in brain ThTP is synthesized in mitochondria by a ], perhaps similar to ].<ref name="Ref5">{{cite journal | doi = 10.1074/jbc.M109.054379 | title = Thiamine Triphosphate Synthesis in Rat Brain Occurs in Mitochondria and is Coupled to the Respiratory Chain | year = 2009 | last1 = Gangolf | first1 = M. | last2 = Wins | first2 = P. | last3 = Thiry | first3 = M. | last4 = El Moualij | first4 = B. | last5 = Bettendorff | first5 = L. | journal = Journal of Biological Chemistry | volume = 285 | pages = 583–94 | pmid = 19906644 | issue = 1 | pmc = 2804207| doi-access = free }}</ref> In ], ThTP is hydrolyzed to ] (ThDP) by a specific ].<ref name="Ref3" /><ref name="Ref7">{{cite journal | doi = 10.1074/jbc.M709675200 | title = Structural Basis for the Catalytic Mechanism of Mammalian 25-kDa Thiamine Triphosphatase | year = 2008 | last1 = Song | first1 = J. | last2 = Bettendorff | first2 = L. | last3 = Tonelli | first3 = M. | last4 = Markley | first4 = J. L. | journal = Journal of Biological Chemistry | volume = 283 | issue = 16 | pages = 10939–48 | pmid = 18276586 | pmc = 2447667| doi-access = free }}</ref> It can also be converted into ThDP by ]. |
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==History== |
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Thiamine triphosphate (ThTP) was chemically synthesized in 1948 at a time when the only organic ] known was ATP.<ref>{{Cite journal |author1=Velluz L., Amiard G. |author2=Bartos J. |name-list-style=amp | year = 1948 |title = Un nouveau derive de phosphorylation de la vitamine=B1, lacide thiamine triphosphorique | journal = J. Bull. Soc. Chim. Fr. | volume = 15 | pages = 871}}</ref> The first claim of the existence of ThTP in living organisms was made in rat liver,<ref>{{Cite journal |author1=Rossi-Fanelli A., Siliprandi N. |author2=Fasella P. |name-list-style=amp | year = 1952 | title = On the presence of triphosphothiamine (TPT) in the liver | journal = Science | volume = 116 | pages = 711–713 | doi = 10.1126/science.116.3026.711 | pmid = 13028255 | issue = 3026|bibcode=1952Sci...116..711R }}</ref> followed by baker’s yeast.<ref>{{Cite journal | author = Kiessling K.-H. | year = 1953 | title = Thiamine triphosphate in baker's yeast | journal = Nature | volume = 172 | pages = 1187–1188 | doi = 10.1038/1721187a0 | pmid = 13111284 | issue = 4391| bibcode = 1953Natur.172.1187K | s2cid = 4289038 }}</ref> Its presence was later confirmed in rat tissues<ref>{{Cite journal |author1=Greiling H. |author2=Kiesow L. |name-list-style=amp | year = 1958 | title = Zur Biochemie der Thiamintriphosphorsäure IV. Das Vorkommen von Thiamintriphosphat im tierischen Organismus | journal = Zeitschrift für Naturforschung B | volume = 13 | pages = 251–252 | doi=10.1515/znb-1958-0412| doi-access = free }}</ref> and in plants germs, but not in seeds, where thiamine was essentially ].<ref>{{Cite journal | author = Yusa T. | year = 1962 | title = Studies on thiamine triphosphate II. Thiamine triphosphate as phosphate donor | journal = Plant Cell | volume = 3 | pages = 95–103}}</ref> In all those studies, ThTP was separated from other thiamine derivatives using a ] method, followed by ] in fluorescent ] compounds with ] in ] solution. This method is at best semi-quantitative, and the development of ] methods suggested that ThTP represents far less than 10% of total thiamine in animal tissues.<ref>{{Cite journal |author1=Rindi G. |author2=de Giuseppe L. |name-list-style=amp | year = 1961 | title = A new chromatographic method for the determination of thiamine and its mono-, di- and triphosphates in animal tissues | journal = Biochem. J. | volume = 78 |issue=3 | pages = 602–606 | pmid = 13741738 | pmc = 1205381 | doi=10.1042/bj0780602}}</ref> |
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== References == |
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