Thiamine triphosphate
| Thiamine triphosphate | |
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| Identifiers | |
| CAS number | 3475-65-8 |
| PubChem | 18989 |
| ChemSpider | 17927  |
| MeSH | Thiamine+triphosphate |
| ChEBI | CHEBI:18284 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C12H19N4O10P3S |
| Molar mass | 504.288 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Thiamine triphosphate (ThTP) is found in most organisms, bacteria, fungi, plants and animals.[1]
Contents |
[edit] Function
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] Moreover some results suggesting that ThTP deficiency is responsible for subacute necrotizing encephalopathy or Leigh's disease have not been confirmed. [4]
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).
[edit] Metabolism
It has been shown that in brain ThTP is synthesized in mitochondria by a chemiosmotic mechanism, perhaps similar to ATP synthase.[5] In mammals, ThTP is hydrolyzed to ThDP by a specific thiamine triphosphatase.[6] [7] It can also be converted into ThDP by thiamine-diphosphate kinase.
[edit] History
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]
[edit] References
- ^ 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 60:1477-1488.
- ^ Matsuda T & Cooper JR. (1981) Thiamine as an integral component of brain synaptosomal membranes. Proc Natl Acad Sci U S A 78:5886-5889. pmid=6272323 pmc=348897
- ^ a b Lakaye B, Wirtzfeld B, Wins P, Grisar T & Bettendorff L. (2004) Thiamine triphosphate, a new signal required for optimal growth of Escherichia coli during amino acid starvation. J Biol Chem 279:17142-17147 pmid=14769791 url=http://www.jbc.org/content/279/17/17142.long
- ^ Cooper JR, Itokawa Y & Pincus JH. (1969) Thiamine triphosphate deficiency in subacute necrotizing encephalomyelopathy. Science 164:74-75 pmid=5773712 url=http://www.sciencemag.org/content/164/3875/74.long
- ^ Gangolf M., Wins P., Thiry M., El Moualij B. & Bettendorff L. (2010) Thiamine triphosphate synthesis in the rat brain is mitochondrial and coupled to the respiratory chain. J Biol Chem 285: 583-594 pmid=19906644 url=http://www.jbc.org/content/285/1/583.long
- ^ Lakaye B., Makarchikov A.F., Fernandes Antunes A., Zorzi W., Coumans B., De Pauw E., Wins P., Grisar T. & Bettendorff L. (2002) Molecular characterization of a specific thiamine triphosphatase widely distributed in mammalian tissues. J Biol Chem 277: 13771-13777 pmid=11827967 url=http://www.jbc.org/content/277/16/13771.long
- ^ Song J., Bettendorff L., Tonelli M. & Markley, J.L. (2008) Structural basis for the catalytic mechanism of mammalian 25 kDa-thiamine triphosphatase. "J Biol Chem 283: 10939-10948 pmid=18276586 url=http://www.jbc.org/content/283/16/10939.long
- ^ Velluz L., Amiard G. & Bartos J. (1948) J. Bull. Soc. Chim. Fr. 15: 871.
- ^ Rossi-Fanelli A., Siliprandi N. & Fasella P. (1952) On the presence of triphosphothiamine (TPT) in the liver. Science 116: 711-713.
- ^ Kiessling K.-H. (1953) Thiamine triphosphate in baker's yeast Nature 172: 1187-1188.
- ^ Greiling H. & Kiesow L. (1958) Zur Biochemie der Thiamintriphosphorsäure IV. Das Vorkommen von Thiamintriphosphat im tierischen Organismus. Z. Naturforschg. 13b: 251-252.
- ^ Yusa T. (1962) Studies on thiamine triphosphate II. Thiamine triphosphate as phosphate donor; Plant cell 3: 95-103.
- ^ 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: 602-606
