Thiamine triphosphate
| Thiamine triphosphate | |
|---|---|
| 200px | |
| Identifiers | |
| CAS number | |
| PubChem | |
| MeSH | |
| SMILES | CC1=C(SC=[N+]1CC2=CN= C(N=C2N)C)CCOP(=O) (O)OP(=O)(O)OP(=O)(O)[O-] |
| Properties | |
| Molecular formula | C12H19N4O10P3S |
| Molar mass | 504.288 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Thiamine triphosphate (ThTP) is found in most organisms, bacteria, fungi, plants and animals.[1]
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).
In mammals, ThTP is hydrolyzed by a specific thiamine triphosphatase.[5]
History
Thiamine triphosphate (ThTP) was chemically synthesized in 1948 at a time when the only organic triphosphate known was ATP.[6]
The first claim of the existence of ThTP in living organisms was made in rat liver,[7] followed by baker’s yeast.[8]
Its presence was later confirmed in rat tissues[9] and in plants germs, but not in seeds, where thiamine was essentially unphosphorylated.[10]
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[11] and bacteria.[12]
References
- ↑ 1.0 1.1 1.2 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):1477-1488.
- ↑ Matsuda T & Cooper JR. (1981) Thiamine as an integral component of brain synaptosomal membranes. Proc Natl Acad Sci U S A 78(9):5886-5889.
- ↑ 3.0 3.1 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(17):17142-17147.
- ↑ Cooper JR, Itokawa Y & Pincus JH. (1969) Thiamine triphosphate deficiency in subacute necrotizing encephalomyelopathy. Science 164(875):74-75.
- ↑ 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.
- ↑ Velluz et al. 1948
- ↑ Rossi-Fanelli et al. 1952
- ↑ Kiessling 1953
- ↑ Greiling and Kiesow 1958
- ↑ Yusa 1961
- ↑ Rindi and Giuseppe 1961
- ↑ Rossi-Fanelli et al. 1961
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