Thiamine triphosphate

Identifiers

CAS Number

* 3475-65-8 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:18284 Y

ChemSpider |

* 17927 Y

MeSH | Thiamine+triphosphate

PubChem CID

* 18989

UNII |

* 464M6AQ7IV Y

CompTox Dashboard (EPA)

* DTXSID80956233

InChI

* InChI=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) Y

Key: IWLROWZYZPNOFC-UHFFFAOYSA-N Y

* 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)

Key: IWLROWZYZPNOFC-UHFFFAOYAE

SMILES

* Cc1c(sc[n+]1Cc2cnc(nc2N)C)CCOP(=O)(O)OP(=O)(O)OP(=O)(O)[O-]

Properties

Chemical formula

| C12H19N4O10P3S
Molar mass | 504.288

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

Chemical compound

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.

## Function[edit]

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] 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).

## Metabolism[edit]

It 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.

## History[edit]

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]

## References[edit]

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): 1477–88. doi:10.1007/s00018-003-3098-4. PMID 12943234. S2CID 25400487.
2. ^ Matsuda, T; Cooper, JR (1981). "Thiamine as an integral component of brain synaptosomal membranes". Proceedings of the National Academy of Sciences of the United States of America. 78 (9): 5886–9. Bibcode:1981PNAS...78.5886M. doi:10.1073/pnas.78.9.5886. PMC 348897. PMID 6272323.
3. ^ a b c Lakaye, B.; Makarchikov, AF; Antunes, AF; Zorzi, W; Coumans, B; De Pauw, E; Wins, P; Grisar, T; Bettendorff, L (2002). "Molecular Characterization of a Specific Thiamine Triphosphatase Widely Expressed in Mammalian Tissues". Journal of Biological Chemistry. 277 (16): 13771–7. doi:10.1074/jbc.M111241200. PMID 11827967.
4. ^ Murphy, J. V.; Craig, L. (1975). "Leigh's disease: Significance of the biochemical changes in brain". Journal of Neurology, Neurosurgery, and Psychiatry. 38 (11): 1100–1103. doi:10.1136/jnnp.38.11.1100. PMC 492163. PMID 1206418.
5. ^ Murphy, Jerome V. (1974). "Leigh Disease". Archives of Neurology. 31 (4): 220. doi:10.1001/archneur.1974.00490400034002.
6. ^ Gangolf, M.; Wins, P.; Thiry, M.; El Moualij, B.; Bettendorff, L. (2009). "Thiamine Triphosphate Synthesis in Rat Brain Occurs in Mitochondria and is Coupled to the Respiratory Chain". Journal of Biological Chemistry. 285 (1): 583–94. doi:10.1074/jbc.M109.054379. PMC 2804207. PMID 19906644.
7. ^ Song, J.; Bettendorff, L.; Tonelli, M.; Markley, J. L. (2008). "Structural Basis for the Catalytic Mechanism of Mammalian 25-kDa Thiamine Triphosphatase". Journal of Biological Chemistry. 283 (16): 10939–48. doi:10.1074/jbc.M709675200. PMC 2447667. PMID 18276586.
8. ^ Velluz L., Amiard G. & Bartos J. (1948). "Un nouveau derive de phosphorylation de la vitamine=B1, lacide thiamine triphosphorique". J. Bull. Soc. Chim. Fr. 15: 871.
9. ^ Rossi-Fanelli A., Siliprandi N. & Fasella P. (1952). "On the presence of triphosphothiamine (TPT) in the liver". Science. 116 (3026): 711–713. Bibcode:1952Sci...116..711R. doi:10.1126/science.116.3026.711. PMID 13028255.
10. ^ Kiessling K.-H. (1953). "Thiamine triphosphate in baker's yeast". Nature. 172 (4391): 1187–1188. Bibcode:1953Natur.172.1187K. doi:10.1038/1721187a0. PMID 13111284. S2CID 4289038.
11. ^ Greiling H. & Kiesow L. (1958). "Zur Biochemie der Thiamintriphosphorsäure IV. Das Vorkommen von Thiamintriphosphat im tierischen Organismus". Zeitschrift für Naturforschung B. 13: 251–252. doi:10.1515/znb-1958-0412.
12. ^ Yusa T. (1962). "Studies on thiamine triphosphate II. Thiamine triphosphate as phosphate donor". Plant Cell. 3: 95–103.
13. ^ 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 (3): 602–606. doi:10.1042/bj0780602. PMC 1205381. PMID 13741738.

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency