Thiamine triphosphate

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ImageFile=ThTP-2D.jpg
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CASNo=3475-65-8
PubChem=18989
SMILES=CC1=C(SC= [N+] 1CC2=CN= C(N=C2N)C)CCOP(=O) (O)OP(=O)(O)OP(=O)(O) [O-]
MeSHName=Thiamine+triphosphate
Section2= Chembox Properties
Formula=C₁₂H₁₉N₄O₁₀P₃S
MolarMass=504.288
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Thiamine triphosphate (ThTP) is found in most organisms, bacteria, fungi, plants and animals.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. ]

Function

It has been proposed that ThTP has a specific role in nerve excitabilityMatsuda T & Cooper JR. (1981) Thiamine as an integral component of brain synaptosomal membranes. "Proc Natl Acad Sci U S A" 78(9):5886-5889. ] but this has never been confirmed and recent results suggest that ThTP probably plays a role in cell energy metabolism. ] 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.] Moreover some results suggesting that ThTP deficiency is responsible for subacute necrotizing encephalopathy or Leigh's disease have not been confirmed. Cooper JR, Itokawa Y & Pincus JH. (1969) Thiamine triphosphate deficiency in subacute necrotizing encephalomyelopathy. "Science" 164(875):74-75.]

In "E. coli", ThTP is accumulated in the presence of glucose during amino acid starvation. ] ] 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.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.]

History

Thiamine triphosphate (ThTP) was chemically synthesized in 1948 at a time when the only organic triphosphate known was ATP. [Velluz et al. 1948]

The first claim of the existence of ThTP in living organisms was made in rat liver, [Rossi-Fanelli et al. 1952] followed by baker’s yeast. [Kiessling 1953]

Its presence was later confirmed in rat tissues [Greiling and Kiesow 1958] and in plants germs, but not in seeds, where thiamine was essentially unphosphorylated. [Yusa 1961]

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 [Rindi and Giuseppe 1961] and bacteria. [Rossi-Fanelli et al. 1961]

References