My watch list  

Thiamine triphosphate

Thiamine triphosphate
CAS number 3475-65-8
PubChem 18989
MeSH Thiamine+triphosphate
SMILES CC1=C(SC=[N+]1CC2=CN= C(N=C2N)C)CCOP(=O) (O)OP(=O)(O)OP(=O)(O)[O-]
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]


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]


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]


  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):1477-1488.
  2. ^ 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. ^ 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(17):17142-17147.
  4. ^ Cooper JR, Itokawa Y & Pincus JH. (1969) Thiamine triphosphate deficiency in subacute necrotizing encephalomyelopathy. Science 164(875):74-75.
  5. ^ 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.
  6. ^ Velluz et al. 1948
  7. ^ Rossi-Fanelli et al. 1952
  8. ^ Kiessling 1953
  9. ^ Greiling and Kiesow 1958
  10. ^ Yusa 1961
  11. ^ Rindi and Giuseppe 1961
  12. ^ Rossi-Fanelli et al. 1961
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Thiamine_triphosphate". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE