词条 | Thiamine triphosphate |
释义 |
| Verifiedfields = changed | verifiedrevid = 470606262 | ImageFile=Thiamintriphosphat.svg | ImageSize= | IUPACName= | OtherNames= |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 17927 | 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) | InChIKey = IWLROWZYZPNOFC-UHFFFAOYAE | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = IWLROWZYZPNOFC-UHFFFAOYSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo=3475-65-8 | PubChem=18989 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 18284 | SMILES = Cc1c(sc[n+]1Cc2cnc(nc2N)C)CCOP(=O)(O)OP(=O)(O)OP(=O)(O)[O-] | MeSHName=Thiamine+triphosphate |Section2={{Chembox Properties | Formula=C12H19N4O10P3S | MolarMass=504.288 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} 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. FunctionIt 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). MetabolismIt 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. HistoryThiamine 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] References1. ^1 2 {{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 }} 2. ^{{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}} 3. ^1 2 {{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 }} 4. ^{{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}} 5. ^{{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. }} 6. ^{{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}} 7. ^{{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}} 8. ^{{Cite journal |author1=Velluz L., Amiard G. |author2=Bartos J. |lastauthoramp=yes | 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}} 9. ^{{Cite journal |author1=Rossi-Fanelli A., Siliprandi N. |author2=Fasella P. |lastauthoramp=yes | 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}} 10. ^{{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}} 11. ^{{Cite journal |author1=Greiling H. |author2=Kiesow L. |lastauthoramp=yes | 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}} 12. ^{{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}} 13. ^{{Cite journal |author1=Rindi G. |author2=de Giuseppe L. |lastauthoramp=yes | 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 | pages = 602–606 | pmid = 13741738 | pmc = 1205381}} 5 : Biomolecules|Organophosphates|Thiazoles|Thiamine|Pyrimidines |
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