Thiamin diphosphate in biological chemistry: New aspects of thiamin metabolism, especially triphosphate derivatives acting other than as cofactors

FEBS Journal

Volumn 276, Issue 11, 2009, Pages 2917-2925

  Bettendorff, Lucien ^a   Wins, Pierre ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

Adenosine thiamin triphosphate; Adenylate kinase; Alarmone; Escherichia coli; Regulation; Riboswitch; Thiamin transport; Thiamin triphosphatase; Thiamin triphosphate; Triphosphate tunnel metalloenzymes

Indexed keywords

AMINO ACID; COCARBOXYLASE; THIAMINE PHOSPHATE; THIAMINE PYROPHOSPHOKINASE; THIAMINE TRIPHOSPHATASE; THIAMINE TRIPHOSPHATE;

BIOSYNTHESIS; CATALYSIS; CONTROLLED STUDY; ENZYME SYNTHESIS; ESCHERICHIA COLI; EUKARYOTIC CELL; HYDROLYSIS; IN VIVO STUDY; METABOLISM; NEUROPHYSIOLOGY; NONHUMAN; NUTRITION; PEROXISOME; PRIORITY JOURNAL; PROKARYOTIC CELL; SHORT SURVEY; SIGNAL TRANSDUCTION; STARVATION; SYNTHESIS;

ADENOSINE TRIPHOSPHATE; ANIMALS; HUMANS; MITOCHONDRIA; MOLECULAR STRUCTURE; PEROXISOMES; THIAMINE; THIAMINE MONOPHOSPHATE; THIAMINE PYROPHOSPHATE; THIAMINE TRIPHOSPHATE;

ANIMALIA; ESCHERICHIA COLI; PROKARYOTA;

EID: 65549167312     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2009.07019.x     Document Type: Short Survey

References (68)

1. Frank RA, Leeper FJ Luisi BF (2007) Structure, mechanism and catalytic duality of thiamin-dependent enzymes. Cell Mol Life Sci 64, 892 905. (Pubitemid 46597755)
2. Breslow R (1958) On the mechanism of thiamin action. IV. Evidence from studies on model systems. J Am Chem Soc 80, 3719 3726.
3. Kale S, Ulas G, Song J, Brudvig GW, Furey W Jordan F (2008) Efficient coupling of catalysis and dynamics in the E1 component of Escherichia coli pyruvate dehydrogenase multienzyme complex. Proc Natl Acad Sci USA 105, 1158 1163.
4. Kluger R Tittmann K (2008) Thiamin diphosphate catalysis: enzymic and nonenzymic covalent intermediates. Chem Rev 108, 1797 1833.
5. Kawasaki T (1992) Vitamin B1: thiamin. In Modern Chromatographic Analysis of Vitamins (De Leenheer AP, Lambert WE Nelis HJ, eds pp. 319 354. Marcel Dekker, New York.
6. Makarchikov AF, Lakaye B, Gulyai IE, Czerniecki J, Coumans B, Wins P, Grisar T Bettendorff L (2003) Thiamin triphosphate and thiamin triphosphatase activities: from bacteria to mammals. Cell Mol Life Sci 60, 1477 1488. (Pubitemid 36900529)
7. 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 thiamin adenine nucleotide. Nat Chem Biol 3, 211 212. (Pubitemid 46440538)
8. Shi Q, Karuppagounder SS, Xu H, Pechman D, Chen H Gibson GE (2007) Responses of the mitochondrial alpha-ketoglutarate dehydrogenase complex to thiamin deficiency may contribute to regional selective vulnerability. Neurochem Int 50, 921 931. (Pubitemid 46962817)
9. 13C nuclear magnetic resonance spectroscopy. J Neurochem 106, 603 612.
10. Karuppagounder SS, Xu H, Shi Q, Chen LH, Pedrini S, Pechman D, Baker H, Beal MF, Gandy SE Gibson GE (2008) Thiamin deficiency induces oxidative stress and exacerbates the plaque pathology in Alzheimer's mouse model. Neurobiol Aging. doi :.
11. Webb ME, Marquet A, Mendel RR, Rebeille F Smith AG (2007) Elucidating biosynthetic pathways for vitamins and cofactors. Nat Prod Rep 24, 988 1008. (Pubitemid 47493397)
12. Begley TP, Chatterjee A, Hanes JW, Hazra A Ealick SE (2008) Cofactor biosynthesis - still yielding fascinating new biological chemistry. Curr Opin Chem Biol 12, 118 125.
13. Murata K (1982) Actions of two types of thiaminase on thiamin and its analogues. Ann NY Acad Sci 378, 146 156. (Pubitemid 12079900)
14. Jenkins AH, Schyns G, Potot S, Sun G Begley TP (2007) A new thiamin salvage pathway. Nat Chem Biol 3, 492 497. (Pubitemid 47080370)
15. Onozuka M, Konno H, Kawasaki Y, Akaji K Nosaka K (2008) Involvement of thiaminase II encoded by the THI20 gene in thiamin salvage of Saccharomyces cerevisiae. FEMS Yeast Res 8, 266 275.
16. Montange RK Batey RT (2008) Riboswitches: emerging themes in RNA structure and function. Annu Rev Biophys 37, 117 133.
17. Winkler W, Nahvi A Breaker RR (2002) Thiamin derivatives bind messenger RNAs directly to regulate bacterial gene expression. Nature 419, 952 956. (Pubitemid 35339632)
18. Mironov AS, Gusarov I, Rafikov R, Lopez LE, Shatalin K, Kreneva RA, Perumov DA Nudler E (2002) Sensing small molecules by nascent RNA. A mechanism to control transcription in bacteria. Cell 111, 747 756. (Pubitemid 35446317)
19. Soriano EV, Rajashankar KR, Hanes JW, Bale S, Begley TP Ealick SE (2008) Structural similarities between thiamin-binding protein and thiaminase-I suggest a common ancestor. Biochemistry 47, 1346 1357.
20. Enjo F, Nosaka K, Ogata M, Iwashima A Nishimura H (1997) Isolation and characterization of a thiamin transport gene, THI10, from Saccharomyces cerevisiae. J Biol Chem 272, 19165 19170. (Pubitemid 27337703)
21. Singleton CK (1997) Identification and characterization of the thiamin transporter gene of Saccharomyces cerevisiae. Gene 199, 111 121. (Pubitemid 27448208)
22. Vogl C, Klein CM, Batke AF, Schweingruber ME Stolz J (2008) Characterization of Thi9, a novel thiamin (vitamin B1) transporter from Schizosaccharomyces pombe. J Biol Chem 283, 7379 7389.
23. Ganapathy V, Smith SB Prasad PD (2004) SLC19: the folate/thiamin transporter family. Pflügers Arch 447, 641 646.
24. Zhao R, Gao F Goldman ID (2002) Reduced folate carrier transports thiamin monophosphate: an alternative route for thiamin delivery into mammalian cells. Am J Physiol Cell Physiol 282, C1512 C1517. (Pubitemid 34663100)
25. Dutta B, Huang W, Molero M, Kekuda R, Leibach FH, Devoe LD, Ganapathy V Prasad PD (1999) Cloning of the human thiamin transporter, a member of the folate transporter family. J Biol Chem 274, 31925 31929. (Pubitemid 129503781)
26. Eudy JD, Spiegelstein O, Barber RC, Wlodarczyk BJ, Talbot J Finnell RH (2000) Identification and characterization of the human and mouse SLC19A3 gene: a novel member of the reduced folate family of micronutrient transporter genes. Mol Genet Metab 71, 581 590. (Pubitemid 32039345)
27. Said HM, Balamurugan K, Subramanian VS Marchant JS (2004) Expression and functional contribution of hTHTR-2 in thiamin absorption in human intestine. Am J Physiol Gastrointest Liver Physiol 286, G491 G498. (Pubitemid 38250322)
28. Fleming JC, Tartaglini E, Steinkamp MP, Schorderet DF, Cohen N Neufeld EJ (1999) The gene mutated in thiamin-responsive anaemia with diabetes and deafness (TRMA) encodes a functional thiamin transporter. Nat Genet 22, 305 308. (Pubitemid 29297261)
29. Nosaka K, Kaneko Y, Nishimura H Iwashima A (1993) Isolation and characterization of a thiamin pyrophosphokinase gene, THI80, from Saccharomyces cerevisiae. J Biol Chem 268, 17440 17447. (Pubitemid 23236986)
30. Bettendorff L, Wins P Lesourd M (1994) Subcellular localization and compartmentation of thiamin derivatives in rat brain. Biochim Biophys Acta 1222, 1 6. (Pubitemid 24163659)
31. Marobbio CM, Vozza A, Harding M, Bisaccia F, Palmieri F Walker JE (2002) Identification and reconstitution of the yeast mitochondrial transporter for thiamin pyrophosphate. EMBO J 21, 5653 5661. (Pubitemid 35315265)
32. Lindhurst MJ, Fiermonte G, Song S, Struys E, De Leonardis F, Schwartzberg PL, Chen A, Castegna A, Verhoeven N, Mathews CK et al. (2006) Knockout of Slc25a19 causes mitochondrial thiamin pyrophosphate depletion, embryonic lethality, CNS malformations, and anemia. Proc Natl Acad Sci USA 103, 15927 15932. (Pubitemid 44657569)
33. Fraccascia P, Sniekers M, Casteels M Van Veldhoven PP (2007) Presence of thiamin pyrophosphate in mammalian peroxisomes. BMC Biochem 8, 10. (Pubitemid 47041866)
34. Sano S, Matsuda Y Nakagawa H (1988) Thiamin pyrophosphatase (nucleoside diphosphatase) in the Golgi apparatus is distinct from microsomal nucleoside diphosphatase. J Biochem 103, 678 681. (Pubitemid 18113174)
35. Sano S, Matsuda Y Nakagawa H (1988) Type B nucleoside-diphosphatase of rat brain. Purification and properties of an enzyme with high thiamin pyrophosphatase activity. Eur J Biochem 171, 231 236. (Pubitemid 18042887)
36. Kawasaki T, Egi Y Sanemori H (1977) Specific thiamin monophosphate phosphohydrolase in Micrococcus denitrificans. J Bacteriol 130, 542 544. (Pubitemid 8086679)
37. Csillik B, Mihaly A, Krisztin-Peva B, Farkas I Knyihar-Csillik E (2008) Mitigation of nociception via transganglionic degenerative atrophy: possible mechanism of vinpocetine-induced blockade of retrograde axoplasmic transport. Ann Anat 190, 140 145.
38. Bettendorff L (1994) Thiamin in excitable tissues: reflections on a non-cofactor role. Metab Brain Dis 9, 183 209. (Pubitemid 24308119)
39. Lakaye B, Wirtzfeld B, Wins P, Grisar T Bettendorff L (2004) Thiamin triphosphate, a new signal required for optimal growth of Escherichia coli during amino acid starvation. J Biol Chem 279, 17142 17147. (Pubitemid 38560470)
40. Bettendorff L, Kolb HA Schoffeniels E (1993) Thiamin triphosphate activates an anion channel of large unit conductance in neuroblastoma cells. J Membr Biol 136, 281 288. (Pubitemid 24005388)
41. Sabirov RZ Okada Y (2005) ATP release via anion channels. Purinergic Signal 1, 311 328.
42. Nghiêm HO, Bettendorff L Changeux JP (2000) Specific phosphorylation of Torpedo 43K rapsyn by endogenous kinase(s) with thiamin triphosphate as the phosphate donor. FASEB J 14, 543 554. (Pubitemid 30143174)
43. Bettendorff L (1994) The compartmentation of phosphorylated thiamin derivatives in cultured neuroblastoma cells. Biochim Biophys Acta 1222, 7 14. (Pubitemid 24163660)
44. Voskoboyev AI, Chernikevich IP Luchko VS (1987) Studies on thiamin diphosphate kinase (EC 2.7.4.15) from brewer's yeast: purification and some properties. Biomed Biochim Acta 46, 3 13. (Pubitemid 17017592)
45. 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)
46. 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)
47. Gigliobianco T, Lakaye B, Makarchikov AF, Wins P Bettendorff L (2008) Adenylate kinase-independent thiamin triphosphate accumulation under severe energy stress in Escherichia coli. BMC Microbiol 8, 16.
48. Makarchikov AF, Wins P, Janssen E, Wieringa B, Grisar T Bettendorff L (2002) Adenylate kinase 1 knockout mice have normal thiamin triphosphate levels. Biochim Biophys Acta 1592, 117 121.
49. Bettendorff L, Michel-Cahay C, Grandfils C, De Rycker C Schoffeniels E (1987) Thiamin triphosphate and membrane-associated thiamin phosphatases in the electric organ of Electrophorus electricus. J Neurochem 49, 495 502. (Pubitemid 17101181)
50. Egi Y, Koyama S, Shikata H, Yamada K Kawasaki T (1986) Content of thiamin phosphate esters in mammalian tissues - an extremely high concentration of thiamin triphosphate in pig skeletal muscle. Biochem Int 12, 385 390. (Pubitemid 16139130)
51. Bettendorff L, Peeters M, Wins P Schoffeniels E (1993) Metabolism of thiamin triphosphate in rat brain: correlation with chloride permeability. J Neurochem 60, 423 434. (Pubitemid 23030934)
52. Barchi RL Braun PE (1972) A membrane-associated thiamin triphosphatase from rat brain. Properties of the enzyme. J Biol Chem 247, 7668 7673.
53. Matsuda T, Tonomura H, Baba A Iwata H (1991) Membrane-associated thiamin triphosphatase in rat skeletal muscle. Int J Biochem 23, 1111 1114.
54. Bettendorff L, Wins P Schoffeniels E (1988) Thiamin triphosphatase from Electrophorus electric organ is anion-dependent and irreversibly inhibited by 4,4′-diisothiocyanostilbene-2,2′disulfonic acid. Biochem Biophys Res Commun 154, 942 947. (Pubitemid 18208054)
55. Hashitani Y Cooper JR (1972) The partial purification of thiamin triphosphatase from rat brain. J Biol Chem 247, 2117 2119.
56. Makarchikov AF Chernikevich IP (1992) Purification and characterization of thiamin triphosphatase from bovine brain. Biochim Biophys Acta 1117, 326 332.
57. 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 thiamin triphosphatase widely expressed in mammalian tissues. J Biol Chem 277, 13771 13777.
58. Iyer LM Aravind L (2002) The catalytic domains of thiamin triphosphatase and CyaB-like adenylyl cyclase define a novel superfamily of domains that bind organic phosphates. BMC Genomics 3, 33. (Pubitemid 39546597)
59. Szyniarowski P, Lakaye B, Czerniecki J, Makarchikov AF, Wins P, Margineanu I, Coumans B, Grisar T Bettendorff L (2005) Pig tissues express a catalytically inefficient 25-kDa thiamin triphosphatase: insight in the catalytic mechanisms of this enzyme. Biochim Biophys Acta 1725, 93 102. (Pubitemid 41169180)
60. Gong C, Smith P Shuman S (2006) Structure-function analysis of Plasmodium RNA triphosphatase and description of a triphosphate tunnel metalloenzyme superfamily that includes Cet1-like RNA triphosphatases and CYTH proteins. RNA 12, 1468 1474. (Pubitemid 44141526)
61. Lima CD, Wang LK Shuman S (1999) Structure and mechanism of yeast RNA triphosphatase: an essential component of the mRNA capping apparatus. Cell 99, 533 543.
62. Keppetipola N, Jain R Shuman S (2007) Novel triphosphate phosphohydrolase activity of Clostridium thermocellum TTM, a member of the triphosphate tunnel metalloenzyme superfamily. J Biol Chem 282, 11941 11949. (Pubitemid 47100686)
63. Song J, Bettendorff L, Tonelli M Markley JL (2008) Structural basis for the catalytic mechanism of mammalian 25-kDa thiamin triphosphatase. J Biol Chem 283, 10939 10948.
64. Lakaye B, Verlaet M, Dubail J, Czerniecki J, Bontems S, Makarchikov AF, Wins P, Piette J, Grisar T Bettendorff L (2004) Expression of 25 kDa thiamin triphosphatase in rodent tissues using quantitative PCR and characterization of its mRNA. Int J Biochem Cell Biol 36, 2032 2041. (Pubitemid 38760032)
65. Kovacevic Z, Fu D Richardson DR (2008) The iron-regulated metastasis suppressor, Ndrg-1: identification of novel molecular targets. Biochim Biophys Acta 1783, 1981 1992.
66. Suryo Rahmanto Y, Dunn L Richardson D (2007) Identification of distinct changes in gene expression after modulation of melanoma tumor antigen p97 (melanotransferrin) in multiple models in vitro and in vivo. Carcinogenesis 26, 2172 2183. (Pubitemid 47543379)
67. Czerniecki J, Chanas G, Verlaet M, Bettendorff L, Makarchikov AF, Leprince P, Wins P, Grisar T Lakaye B (2004) Neuronal localization of the 25-kDa specific thiamin triphosphatase in rodent brain. Neuroscience 125, 833 840. (Pubitemid 38553891)
68. Makarchikov AF, Brans A Bettendorff L (2007) Thiamin diphosphate adenylyl transferase from E. coli: functional characterization of the enzyme synthesizing adenosine thiamin triphosphate. BMC Biochem 8, 17. (Pubitemid 47397421)