チアミン三リン酸
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- vitaminB1
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/05 20:20:40」(JST)
[Wiki en表示]
| Thiamine triphosphate |
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| Identifiers |
| CAS number |
3475-65-8 |
| PubChem |
18989 |
| ChemSpider |
17927 Y |
| MeSH |
Thiamine+triphosphate |
| ChEBI |
CHEBI:18284 Y |
| Jmol-3D images |
Image 1 |
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Cc1c(sc[n+]1Cc2cnc(nc2N)C)CCOP(=O)(O)OP(=O)(O)OP(=O)(O)[O-]
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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
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| Properties |
| Molecular formula |
C12H19N4O10P3S |
| Molar mass |
504.288 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| Y (verify) (what is: Y/N?) |
| Infobox references |
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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.
Contents
- 1 Function
- 2 Metabolism
- 3 History
- 4 References
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).
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 thiamine pyrophosphate (ThDP) by a specific thiamine-triphosphatase.[3][6] It can also be converted into ThDP by thiamine-diphosphate kinase.
History
Thiamine triphosphate (ThTP) was chemically synthesized in 1948 at a time when the only organic triphosphate known was ATP.[7] The first claim of the existence of ThTP in living organisms was made in rat liver,[8] followed by baker’s yeast.[9] Its presence was later confirmed in rat tissues[10] and in plants germs, but not in seeds, where thiamine was essentially unphosphorylated.[11] 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.[12]
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 (7): 1477–1488. doi:10.1007/s00018-003-3098-4. PMID 12943234.
- ^ 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. doi:10.1073/pnas.78.9.5886. PMC 348897. PMID 6272323.
- ^ 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.
- ^ Cooper, J. R.; Itokawa, Y.; Pincus, J. H. (1969). "Tbiamine-Triphosphate Deficiency in Subacute Necrotizing Encephalomyelopathy". Science 164 (3875): 74–5. doi:10.1126/science.164.3875.74. PMID 5773712.
- ^ 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.
- ^ 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.
- ^ 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 (3026): 711–713. doi:10.1126/science.116.3026.711. PMID 13028255.
- ^ Kiessling K.-H. (1953). "Thiamine triphosphate in baker's yeast". Nature 172 (4391): 1187–1188. doi:10.1038/1721187a0. PMID 13111284.
- ^ 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. PMC 1205381. PMID 13741738.
UpToDate Contents
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English Journal
- Structural Determinants of Specificity and Catalytic Mechanism in mammalian 25-kDa Thiamine Triphosphatase.
- Delvaux D, Kerff F, Murty MR, Lakaye B, Czerniecki J, Kohn G, Wins P, Herman R, Gabelica V, Heuze F, Tordoir X, Marée R, Matagne A, Charlier P, De Pauw E, Bettendorff L.SourceGIGA-Neurosciences, Université de Liège, Avenue de l'Hôpital 1, B-4000 Liège, Belgium.
- Biochimica et biophysica acta.Biochim Biophys Acta.2013 May 22. pii: S0304-4165(13)00210-9. doi: 10.1016/j.bbagen.2013.05.014. [Epub ahead of print]
- BACKGROUND: Thiamine triphosphate (ThTP) is present in most organisms and might be involved in intracellular signaling. In mammalian cells, the cytosolic ThTP level is controlled by a specific thiamine triphosphatase (ThTPase), belonging to the CYTH superfamily of proteins. CYTH proteins are present
- PMID 23707715
- An alternative role of FoF1-ATP synthase in Escherichia coli: synthesis of thiamine triphosphate.
- Gigliobianco T, Gangolf M, Lakaye B, Pirson B, von Ballmoos C, Wins P, Bettendorff L.SourceUnit of Bioenergetics and Cerebral Excitability, GIGA-Neurosciences, University of Liège, Liège, Belgium.
- Scientific reports.Sci Rep.2013;3:1071. doi: 10.1038/srep01071. Epub 2013 Jan 15.
- In E. coli, thiamine triphosphate (ThTP), a putative signaling molecule, transiently accumulates in response to amino acid starvation. This accumulation requires the presence of an energy substrate yielding pyruvate. Here we show that in intact bacteria ThTP is synthesized from free thiamine diphosp
- PMID 23323214
- [Drug with a high metabolic activity, cocarnit, in the treatment of diabetic cardiac autonomic neuropathy].
- Popov SV, Melekhovets' OK, Demikhova NV, Vynnychenko LB.AbstractLeft ventricular diastolic dysfunction in patients with diabetes is formed in the absence of atherosclerotic changes as a consequence of diabetic cardiac autonomic neuropathy in the early stages of diabetes. Progression of autonomic cardiac neuropathy in cardio-vascular type is associated with the violation of energy supply of cells, protein synthesis, electrolyte exchange, the exchange of trace elements, oxidation reduction processes, oxygen-transport function of blood, so that metabolic therapy is carried out to optimize the processes of formation and energy costs. The drug cocarnit activates processes of aerobic oxidation of glucose, as well as providing regulatory influence on the oxidation of fatty acids. Applying of cocarnit in complex therapy in patients with diabetic cardiac autonomic neuropathy found improvement of left ventricular diastolic function, and positive dynamics in the efferent activity balance of the sympathetic and parasympathetic control of heart rate variability, which provides the regression of clinical symptoms.
- Likars'ka sprava / Ministerstvo okhorony zdorov'ia Ukraïny.Lik Sprava.2012 Apr-Jun;(3-4):75-81.
- Left ventricular diastolic dysfunction in patients with diabetes is formed in the absence of atherosclerotic changes as a consequence of diabetic cardiac autonomic neuropathy in the early stages of diabetes. Progression of autonomic cardiac neuropathy in cardio-vascular type is associated with the v
- PMID 23356142
Japanese Journal
- Adenosine Thiamine Triphosphate (AThTP) Inhibits Poly(ADP-Ribose) Polymerase-1 (PARP-1) Activity
- Journal of nutritional science and vitaminology 57(2), 192-196, 2011-04-01
- NAID 10030029043
- ST-segment Elevation of Electrocardiogram in a Patient with Shoshin Beriberi
Related Links
- Thiamine Triphosphate information including symptoms, causes, diseases, symptoms, treatments, and other medical and health issues.
- What does thiamine triphosphate mean? Information and translations of thiamine triphosphate in the most comprehensive dictionary definitions resource on the web.
★リンクテーブル★
[★]
- 英
- thiamine triphosphate TTP
[★]
三リン酸エステル、三リン酸塩、三リン酸
- 関
- trisphosphate
[★]
ビタミンB1、チアミン, thiamine