Thiaminylated adenine nucleotides. Chemical synthesis, structural characterization and natural occurrence

FEBS Journal

Volumn 276, Issue 12, 2009, Pages 3256-3268

  Frédérich, Michel ^a   Delvaux, David ^a   Gigliobianco, Tiziana ^a   Gangolf, Marjorie ^a   Dive, Georges ^a   Mazzucchelli, Gabriel ^a   Elias, Benjamin ^b   De Pauw, Edwin ^a   Angenot, Luc ^a   Wins, Pierre ^a   Bettendorff, Lucien ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Adenosine hiamine riphosphate; Adenosine thiamine diphosphate; Cofactor; Metabolism; Nucleotides

Indexed keywords

ADENINE NUCLEOTIDE; COCARBOXYLASE; PHOSPHATE; THIAMINE DERIVATIVE; THIAMINE TRIPHOSPHATE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL CULTURE; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; ENERGY METABOLISM; ESCHERICHIA COLI; EUKARYOTIC CELL; FLUOROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MOLECULAR MODEL; MOUSE; NONHUMAN; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTEIN PURIFICATION; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

3T3 CELLS; ADENINE; ADENOSINE DIPHOSPHATE; ADENOSINE TRIPHOSPHATE; ANIMALS; BRAIN CHEMISTRY; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESCHERICHIA COLI; FIBROBLASTS; HUMANS; KIDNEY; LIVER; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MUSCLE, SKELETAL; MYOCARDIUM; QUAIL; SPECTROMETRY, FLUORESCENCE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; THIAMINE PYROPHOSPHATE; THIAMINE TRIPHOSPHATE;

ESCHERICHIA COLI; EUKARYOTA; MAMMALIA; VERTEBRATA;

EID: 66249102639     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2009.07040.x     Document Type: Article

References (35)

1. 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, 1477 1488. (Pubitemid 36900529)
2. Nghiêm HO, Bettendorff L Changeux JP (2000) Specific phosphorylation of Torpedo 43K rapsyn by endogenous kinase(s) with thiamine triphosphate as the phosphate donor. FASEB J 14, 543 554. (Pubitemid 30143174)
3. 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, 17142 17147. (Pubitemid 38560470)
4. Gigliobianco T, Lakaye B, Makarchikov AF, Wins P Bettendorff L (2008) Adenylate kinase-independent thiamine triphosphate accumulation under severe energy stress in Escherichia coli. BMC Microbiol 8, 16.
5. Bettendorff L, Wirtzfeld B, Makarchikov AF, Mazzucchelli G, Frédérich M, Gigliobianco T, Gangolf M, De Pauw E, Angenot L Wins P (2007) Discovery of a natural thiamine adenine nucleotide. Nat Chem Biol 3, 211 212. (Pubitemid 46440538)
6. Makarchikov AF, Brans A Bettendorff L (2007) Thiamine diphosphate adenylyl transferase from E. coli: functional characterization of the enzyme synthesizing adenosine thiamine triphosphate. BMC Biochem 8, 17. (Pubitemid 47397421)
7. Kyowa Hakko Kogyo Co Ltd (1969) Process for Preparing Thiamine Adenine Dinucleotide. United States Patent Office No. 3,474,002.
8. Sankyo Company Ltd (1970) Process for Preparing Thiamine Derivatives. United States Patent Office No. 3,507,854.
9. 32P-labeled or unlabeled nucleoside 5(′)-triphosphates and thiamine triphosphate. Anal Biochem 322, 190 197. (Pubitemid 37330073)
10. Breslow R (1958) On the mechanism of thiamine action. IV. 1 Evidence from studies on model systems. J Am Chem Soc 80, 3719 3726.
11. Chauvet-Monges AM, Rogeret C, Briand C Crevat A (1973) NMR study of the lability of the thiazolium proton in thiamin and its polyphosphoric esters. Biochim Biophys Acta 304, 748 752.
12. Ishii K, Sarai K, Sanemori H Kawasaki T (1979) Analysis of thiamine and its phosphate esters by high-performance liquid chromatography. Anal Biochem 97, 191 195. (Pubitemid 9245534)
13. Lewin LM Wei R (1966) Microassay of thiamine and its phosphate esters after separation by paper chromatography. Anal Biochem 16, 29 35.
14. Baker JC Jacobson MK (1986) Alteration of adenyl dinucleotide metabolism by environmental stress. Proc Natl Acad Sci USA 83, 2350 2352. (Pubitemid 16026884)
15. Miras-Portugal MT, Gualix J, Mateo J, Diaz-Hernandez M, Gomez-Villafuertes R, Castro E Pintor J (1999) Diadenosine polyphosphates, extracellular function and catabolism. Prog Brain Res 120, 397 409. (Pubitemid 29457038)
16. Kisselev LL, Justesen J, Wolfson AD Frolova LY (1998) Diadenosine oligophosphates (Ap(n)A), a novel class of signalling molecules? FEBS Lett 427, 157 163. (Pubitemid 28225049)
17. Lee PC, Bochner BR Ames BN (1983) Diadenosine 5′,5‴-P1,P4- tetraphosphate and related adenylylated nucleotides in Salmonella typhimurium. J Biol Chem 258, 6827 6834.
18. Plateau P Blanquet S (1994) Dinucleoside oligophosphates in micro-organisms. Adv Microb Physiol 36, 81 109. (Pubitemid 24090429)
19. Ishii K, Sarai K, Sanemori H Kawasaki T (1979) Concentrations of thiamine and its phosphate esters in rat tissues determined by high-performance liquid chromatography. J Nutr Sci Vitaminol (Tokyo) 25, 517 523.
20. Sanemori H, Ueki H Kawasaki T (1980) Reversed-phase high-performance liquid chromatographic analysis of thiamine phosphate esters at subpicomole levels. Anal Biochem 107, 451 455. (Pubitemid 11220252)
21. Iwata H, Matsuda T Tonomura H (1988) Improved high-performance liquid chromatographic determination of thiamine and its phosphate esters in animal tissues. J Chromatogr 450, 317 323.
22. Matsuda T, Tonomura H, Baba A Iwata H (1989) Tissue difference in cellular localization of thiamine phosphate esters. Comp Biochem Physiol B 94, 405 409.
23. Voskoboev AI Luchko VS (1980) Isolation and radiometric determination of rat liver ATP:thiamine diphosphate phosphotransferase activity. Vopr Med Khim 26, 564 568.
24. Chernikevich IP, Luchko V, Voskoboev AI Ostrovsky YM (1984) Purification and properties of ATP:thiamine diphosphate phosphotransferase from brewer's yeast. Biokhimiya 49, 899 907.
25. Shikata H, Koyama S, Egi Y, Yamada K Kawasaki T (1989) Cytosolic adenylate kinase catalyzes the synthesis of thiamin triphosphate from thiamin diphosphate. Biochem Int 18, 933 941. (Pubitemid 19165956)
26. Miyoshi K, Egi Y, Shioda T Kawasaki T (1990) Evidence for in vivo synthesis of thiamin triphosphate by cytosolic adenylate kinase in chicken skeletal muscle. J Biochem (Tokyo) 108, 267 270. (Pubitemid 20234516)
27. Bettendorff L, Peeters M, Wins P Schoffeniels E (1993) Metabolism of thiamine triphosphate in rat brain: correlation with chloride permeability. J Neurochem 60, 423 434. (Pubitemid 23030934)
28. Bettendorff L (1994) Thiamine in excitable tissues: reflections on a non-cofactor role. Metab Brain Dis 9, 183 209. (Pubitemid 24308119)
29. Singleton CK Martin PR (2001) Molecular mechanisms of thiamine utilization. Curr Mol Med 1, 197 207. (Pubitemid 33772043)
30. Bâ A (2008) Metabolic and structural role of thiamine in nervous tissues. Cell Mol Neurobiol 28, 923 931.
31. Bettendorff L Wins P (2009) Thiamin diphosphate in biological chemistry: new aspects of thiamin metabolism, especially triphosphate derivatives acting other than as cofactors. FEBS J 276, doi:.
32. Bettendorff L, Peeters M, Jouan C, Wins P Schoffeniels E (1991) Determination of thiamin and its phosphate esters in cultured neurons and astrocytes using an ion-pair reversed-phase high-performance liquid chromatographic method. Anal Biochem 198, 52 59.
33. Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98, 5648 5652.
34. Hariharan PC Pople JA (1973) The influence of polarization functions on molecular hydrogenation energies. Theor Chim Acta 28, 213 217.
35. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC et al. (2004) Gaussian 03, Revision C.02. Gaussian, Inc., Wallingford, CT.