The queuine micronutrient: Charting a course from microbe to man

Nutrients

Volumn 7, Issue 4, 2015, Pages 2897-2929

  Fergus, Claire ^a   Barnes, Dominic ^a   Alqasem, Mashael A ^a   Kelly, Vincent P ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Gut flora; Micronutrient; Queuine; Queuosine; Tetrahydrobiopterin; Transfer RNA; Translation; Tyrosine

Indexed keywords

QUEUINE; QUEUOSINE; QUEUOSINE MODIFIED TRANSFER RNA; TETRAHYDROBIOPTERIN; TRANSFER RNA; TYROSINE; UNCLASSIFIED DRUG; GUANINE; TRACE ELEMENT;

AMINO ACID DEFICIENCY; ANTICODON; ENZYME ACTIVITY; HUMAN; INTESTINE FLORA; NEOPLASM; NONHUMAN; NUTRIENT UPTAKE; REVIEW; RIBOSOMAL FRAMESHIFTING; RNA PROCESSING; RNA STRUCTURE; RNA TRANSLATION; AGING; ANALOGS AND DERIVATIVES; ANIMAL; DISEASE MODEL; GASTROINTESTINAL TRACT; METABOLISM; MICROBIOLOGY; MITOCHONDRION; NEOPLASMS; PUBLICATION;

ANIMALIA; BACTERIA (MICROORGANISMS); EUKARYOTA;

AGING; ANIMALS; DISEASE MODELS, ANIMAL; GASTROINTESTINAL MICROBIOME; GASTROINTESTINAL TRACT; GUANINE; HUMANS; MICRONUTRIENTS; MITOCHONDRIA; NEOPLASMS; NUCLEOSIDE Q; RNA, TRANSFER; TRANSLATIONS;

EID: 84927945449     PISSN: None     EISSN: 20726643     Source Type: Journal    
DOI: 10.3390/nu7042897     Document Type: Review

References (157)

1. Grosjean, H. Nucleic acids are not boring long polymers of only four types of nucleotides: A guided tour. In DNA and RNA Modification Enzymes: Structure, Mechanism, Function and Evolution; Grosjean, H., Ed.; Landes Bioscience: Austen, TX, USA, 2009; pp. 1-18.
2. The RNA Modification Database. Available online: http://mods.rna.albany.edu/home (accessed on 9 April 2015).
3. Iwata-Reuyl, D. Biosynthesis of the 7-deazaguanosine hypermodified nucleosides of transfer RNA. Bioorg. Chem. 2003, 31, 24-43.
4. Agris, P.F. Decoding the genome: A modified view. Nucleic Acids Res. 2004, 32, 223-238.
5. RajBhandary, U.L.; Ghosh, H.P. Studies on polynucleotides. XCI. Yeast methionine transfer ribonucleic acid: Purification, properties, and terminal nucleotide sequences. J. Biol. Chem. 1969, 244, 1104-1113.
6. Goodman, H.M.; Abelson, J.; Landy, A.; Brenner, S.; Smith, J.D. Amber suppression: A nucleotide change in the anticodon of a tyrosine transfer RNA. Nature 1968, 217, 1019-1024.
7. Doctor, B.P.; Loebel, J.E.; Sodd, M.A.; Winter, D.B. Nucleotide sequence of E. coli tyrosine transfer ribonucleic acid. Science 1969, 163, 693-695.
8. Harada, F.; Nishimura, S. Possible anticodon sequences of tRNA His, tRNA Asn, and tRNA Asp from E. coli Universal presence of nucleoside Q in the first position of the anticodons of these transfer ribonucleic acids. Biochemistry 1972, 11, 301-308.
9. Nishimura, S. Structure, biosynthesis, and function of queuosine in transfer RNA. Prog. Nucleic Acid Res. Mol. Biol. 1983, 28, 49-73.
10. Randerath, E.; Agrawal, H.P.; Randerath, K. Specific lack of the hypermodified nucleoside, queuosine, in hepatoma mitochondrial aspartate transfer RNA and its possible biological significance. Cancer Res. 1984, 44, 1167-1171.
11. Mörl, M.; Dörner, M.; Pääbo, S. C to U editing and modifications during the maturation of the mitochondrial tRNA Asp in marsupials. Nucleic Acids Res. 1995, 23, 3380-3384.
12. Ishitani, R.; Nureki, O.; Nameki, N.; Okada, N.; Nishimura, S.; Yokoyama, S. Alternative tertiary structure of tRNA for recognition by a posttranscriptional modification enzyme. Cell 2003, 113, 383-394.
13. Stengl, B.; Meyer, E.A.; Heine, A.; Brenk, R.; Diederich, F.; Klebe, G. Crystal structures of tRNA-guanine transglycosylase (TGT) in complex with novel and potent inhibitors unravel pronounced induced-fit adaptations and suggest dimer formation upon substrate binding. J. Mol. Biol. 2007, 370, 492-511.
14. Phillips, G.; de Crécy-Lagard, V. Biosynthesis and function of tRNA modifications in Archaea. Curr. Opin. Microbiol. 2011, 14, 335-341.
15. Kasai, H.; Nakanishi, K.; Macfarlane, R.D.; Torgerson, D.F.Z.; Ohashi, J.A.; McCloskey, H.J.; Gross, S. The structure of Q-nucleoside isolated from rabbit liver transfer ribonucleic acid. J. Am. Chem. Soc. 1976, 98, 5044-5046.
16. Okada, N.; Shindo-Okada, N.; Nishimura, S. Isolation of mammalian tRNAAsp and tRNATyr by lectin-Sepharose affinity column chromatography. Nucleic Acids Res. 1977, 4, 415-423.
17. Salazar, J.C.; Ambrogelly, A.; Crain, P.F.; McCloskey, J.A.; Söll, D. A truncated aminoacyl-tRNA synthetase modifies RNA. Proc. Natl. Acad. Sci. USA 2004, 101, 7536-7541.
18. Blaise, M.; Olieric, V.; Sauter, C.; Lorber, B.; Roy, B.; Karmakar, S.; Banerjee, R.; Becker, H.D.; Kern, D. Crystal structure of glutamyl-queuosine tRNAAsp synthetase complexed with L-glutamate: structural elements mediating tRNA-independent activation of glutamate and glutamylation of tRNAAsp anticodon. J. Mol. Biol. 2008, 381, 1224-1237.
19. Iwata-Reuyl, D.; de Crécy-Lagard, V. Enzymatic Formation of the 7-Deazaguanosine Hypermodified Nucleosides of tRNA. In DNA and RNA Modification Enzymes: Structure, Mechanism, Function and Evolution; Henri, G., Ed.; Landes Bioscience: Austen, Texas, USA, 2009; pp. 377-391.
20. El Yacoubi, B.; Bailly, M.; de Crécy-Lagard, V. Biosynthesis and function of posttranscriptional modifications of transfer RNAs. Annu. Rev. Genet. 2012, 46, 69-95.
21. Okada, N.; Nishimura, S. Isolation and characterization of a guanine insertion enzyme, a specific tRNA transglycosylase, from E. coli. J. Biol. Chem. 1979, 254, 3061-3066.
22. Ohgi, T.; Goto, T.; Kasai, H.; Nishimura, S. Stereochemistry of the cyclopentene side chain in the nucleoside Q obtained from E. coli tRNA. Tetrahedron Lett. 1976, 17, 367-370.
23. Reyniers, J.P.; Pleasants, J.R.; Wostmann, B.S.; Katze, J.R.; Farkas, W.R. Administration of exogenous queuine is essential for the biosynthesis of the queuosine-containing transfer RNAs in the mouse. J. Biol. Chem. 1981, 256, 11591-11594.
24. Katze, J.R.; Gündüz, U.; Smith, D.L.; Cheng, C.S.; McCloskey, J.A. Evidence that the nucleic acid base queuine is incorporated intact into tRNA by animal cells. Biochemistry 1984, 23, 1171-1176.
25. Ott, G.; Kersten, H.; Nishimura, S. Dictyostelium discoideum: A useful model system to evaluate the function of queuine and of the Q-family of tRNAs. FEBS Lett. 1982, 146, 311-314.
26. Kirtland, G.M.; Morris, T.D.; Moore, P.H.; O'Brian, J.J.; Edmonds, C.G.; McCloskey, J.A.; Katze, J.R. Novel salvage of queuine from queuosine and absence of queuine synthesis in Chlorella pyrenoidosa and Chlamydomonas reinhardtii. J. Bacteriol. 1988, 170, 5633-5641.
27. Siard, T.J.; Jacobson, K.B.; Farkas, W.R. Queuine metabolism and cadmium toxicity in Drosophila melanogaster. Biofactors 1991, 3, 41-47.
28. Gaur, R.; Björk, G.R.; Tuck, S.; Varshney, U. Diet-dependent depletion of queuosine in tRNAs in Caenorhabditis elegans does not lead to a developmental block. J. Biosci. 2007, 32, 747-754.
29. Katze, J.R.; Farkas, W.R. A factor in serum and amniotic fluid is a substrate for the tRNA-modifying enzyme tRNA-guanine transferase. Proc. Nat. Acad. Sci. USA 1979, 76, 3271-3275.
30. Katze, J.R. Queuosine metabolism: possible relation to B-cell activation by C8 derivatives of guanosine. Proc. Soc. Exp. Biol. Med. 1985, 179, 492-496.
31. Kersten, H.; Kersten, W. Part B: Biological Roles and Function of Modification. In Chromatography and Modification of Nucleosides; Gehrke, C.W.; Kuo, K.C.T., Eds.; Elsevier: Amsterdam, The Netherlands, 1990; pp. B69-B108.
32. Katze, J.R.; Basile, B.; McCloskey, J.A. Queuine, a modified base incorporated post-transcriptionally into eukaryotic transfer RNA: Wide distribution in nature. Science 1982, 216, 55-56.
33. Brooks, A.F. Synthesis of Tritium Labeled Queuine, PreQ1 and Related Azide Probes Toward Examining the Prevalence of Queuine. Ph.D. Thesis, University of Michigan,Michigan, MI, USA, June 2012.
34. Palmer, M.T.; Kirkman, R.; Kosloff, B.R.; Eipers, P.G.; Morrow, C.D. tRNA isoacceptor preference prior to retrovirus Gag-Pol junction links primer selection and viral translation. J. Virol. 2007, 81, 4397-4404.
35. Noguchi, S.; Nishimura, Y.; Hirota, Y.; Nishimura, S. Isolation and characterization of an Escherichia coli mutant lacking tRNA-guanine transglycosylase. Function and biosynthesis of queuosine in tRNA. J. Biol. Chem. 1982, 257, 6544-6550.
36. Dineshkumar, T.K.; Thanedar, S.; Subbulakshmi, C.; Varshney, U. An unexpected absence of queuosine modification in the tRNAs of an E. coli B strain. Microbiology 2002, 148, 3779-3787.
37. Katze, J.R.; Beck, W.T.; Cheng, C.S.; McCloskey, J.A. Why is tumor tRNA hypomodified with respect to Q nucleoside? Recent Results Cancer Res. 1983, 84, 140-159.
38. Elliott, M.S.; Katze, J.R.; Trewyn, R.W. Relationship between a tumor promoter-induced decrease in queuine modification of transfer RNA in normal human cells and the expression of an altered cell phenotype. Cancer Res. 1984, 44, 3215-3219.
39. Elliott, M.S.; Trewyn, R.W.; Katze, J.R. Inhibition of queuine uptake in cultured human fibroblasts by phorbol-12,13-didecanoate. Cancer Res. 1985, 45, 1079-1085.
40. Morris, R.C.; Galicia, M.C.; Clase, K.L.; Elliott, M.S. Determination of queuosine modification system deficiencies in cultured human cells. Mol. Genet. Metab. 1999, 68, 56-67.
41. Elliott, M.S.; Crane, D.L. Protein kinase C modulation of queuine uptake in cultured human fibroblasts. Biochem. Biophys. Res. Commun. 1990, 171, 393-400.
42. Morris, R.C.; Brooks, B.J.; Hart, K.L.; Elliott, M.S. Modulation of queuine uptake and incorporation into tRNA by protein kinase C and protein phosphatase. Biochim. Biophys. Acta 1996, 1311, 124-132.
43. Gündüz, U.; Katze, J.R. Queuine salvage in mammalian cells. Evidence that queuine is generated from queuosine 5′-phosphate. J. Biol. Chem. 1984, 259, 1110-1113.
44. Farkas, W.R.; Jacobson, K.B.; Katze, J.R. Substrate and inhibitor specificity of tRNA-guanine ribosyltransferase. Biochim. Biophys. Acta 1984, 781, 64-75.
45. Elliott, M.S.; Katze, J.R. Inhibition of queuine uptake in diploid human fibroblasts by phorbol-12,13-didecanoate. Requirement for a factor derived from early passage cells. J. Biol. Chem. 1986, 261, 13019-13025.
46. Trewyn, R.W.; Gatz, H.B. Altered growth properties of normal human cells induced by phorbol 12,13-didecanoate. In Vitro 1984, 20, 409-415.
47. Elliott, M.S.; Crane, D.L. Interferon induced inhibition of queuine uptake in cultured human fibroblasts. Biochem. Biophys. Res. Commun. 1990, 171, 384-392.
48. Singhal, R.P.; Kopper, R.A.; Nishimura, S.; Shindo-Okada, N. Modification of guanine to queuine in transfer RNAs during development and aging. Biochem. Biophys. Res. Commun. 1981, 99, 120-126.
49. Landin, R.M.; Boisnard, M.; Petrissant, G. Correlation between the presence of tRNA His GUG and the erythropoietic function in foetal sheep liver. Nucleic Acids Res. 1979, 7, 1635-1648.
50. Costa, A.; Païs de Barros, J.P.; Keith, G.; Baranowski, W.; Desgrès, J. Determination of queuosine derivatives by reverse-phase liquid chromatography for the hypomodification study of Q-bearing tRNAs from various mammal liver cells. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2004, 801, 237-247.
51. Jiménez, E.; Marín, M.L.; Martín, R.; Odriozola, J.M.; Olivares, M.; Xaus, J.; Fernández, L.; Rodríguez, J.M. Is meconium from healthy newborns actually sterile? Res. Microbiol. 2008, 159, 187-193.
52. Carbon, P.; Haumont, E.; Fournier, M.; de Henau, S.; Grosjean, H. Site-directed in vitro replacement of nucleosides in the anticodon loop of tRNA: application to the study of structural requirements for queuine insertase activity. EMBO J. 1983, 2, 1093-1097.
53. Howes, N.K.; Farkas, W.R. Studies with a homogeneous enzyme from rabbit erythrocytes catalyzing the insertion of guanine into tRNA. J. Biol. Chem. 1978, 253, 9082-9087.
54. Slany, R.K.; Müller, S.O. tRNA-guanine transglycosylase from bovine liver. Purification of the enzyme to homogeneity and biochemical characterization. Eur. J. Biochem. 1995, 230, 221-228.
55. Shindo-Okada, N.; Okada, N.; Ohgi, T.; Goto, T.; Nishimura, S. Transfer ribonucleic acid guanine transglycosylase isolated from rat liver. Biochemistry 1980, 19, 395-400.
56. Walden, T.L.; Howes, N.; Farkas, W.R. Purification and properties of guanine, queuine-tRNA transglycosylase from wheat germ. J. Biol. Chem. 1982, 257, 13218-13222.
57. Morris, R.C.; Elliott, M.S. Queuosine modification of tRNA: A case for convergent evolution. Mol. Genet. Metab. 2001, 74, 147-159.
58. Deshpande, K.L.; Katze, J.R. Characterization of cDNA encoding the human tRNA-guanine transglycosylase (TGT) catalytic subunit. Gene 2001, 265, 205-212.
59. Gündüz, U.; Elliott, M.S.; Seubert, P.H.; Houghton, J.A.; Houghton, P.J.; Trewyn, R.W.; Katze, J.R. Absence of tRNA-guanine transglycosylase in a human colon adenocarcinoma cell line. Biochim. Biophys. Acta 1992, 1139, 229-238.
60. Boland, C.; Hayes, P.; Santa-Maria, I.; Nishimura, S.; Kelly, V.P. Queuosine formation in eukaryotic tRNA occurs via a mitochondria-localized heteromeric transglycosylase. J. Biol. Chem. 2009, 284, 18218-18227.
61. Romier, C.; Reuter, K.; Suck, D.; Ficner, R. Mutagenesis and crystallographic studies of Zymomonas mobilis tRNA-guanine transglycosylase reveal aspartate 102 as the active site nucleophile. Biochemistry 1996, 35, 15734-15739.
62. Xie, W.; Liu, X.; Huang, R.H. Chemical trapping and crystal structure of a catalytic tRNA guanine transglycosylase covalent intermediate. Nat. Struct. Biol. 2003, 10, 781-788.
63. Chen, Y.C.; Kelly, V.P.; Stachura, S.V.; Garcia, G.A. Characterization of the human tRNA-guanine transglycosylase: Confirmation of the heterodimeric subunit structure. RNA 2010, 16, 958-968.
64. Chen, Y.C.; Brooks, A.F.; Goodenough-Lashua, D.M.; Kittendorf, J.D.; Showalter, H.D.; Garcia, G.A. Evolution of eukaryal tRNA-guanine transglycosylase: Insight gained from the heterocyclic substrate recognition by the wild-type and mutant human and E. coli tRNA-guanine transglycosylases. Nucleic Acids Res. 2011, 39, 2834-2844.
65. Kittendorf, J.D.; Sgraja, T.; Reuter, K.; Klebe, G.; Garcia, G.A. An essential role for aspartate 264 in catalysis by tRNA-guanine transglycosylase from E. coli. J. Biol. Chem. 2003, 278, 42369-42376.
66. Garcia, G.A.; Chervin, S.M.; Kittendorf, J.D. Identification of the rate-determining step of tRNA-guanine transglycosylase from E. coli. Biochemistry 2009, 48, 11243-11251.
67. Romier, C.; Meyer, J.E.; Suck, D. Slight sequence variations of a common fold explain the substrate specificities of tRNA-guanine transglycosylases from the three kingdoms. FEBS Lett. 1997, 416, 93-98.
68. Biela, I.; Tidten-Luksch, N.; Immekus, F.; Glinca, S.; Nguyen, T.X.; Gerber, H.D.; Heine, A.; Klebe, G.; Reuter, K. Investigation of specificity determinants in bacterial tRNA-guanine transglycosylase reveals queuine, the substrate of its eukaryotic counterpart, as inhibitor. PLoS ONE 2013, 8, e64240.
69. Brenk, R.; Stubbs, M.T.; Heine, A.; Reuter, K.; Klebe, G. Flexible adaptations in the structure of the tRNA-modifying enzyme tRNA-guanine transglycosylase and their implications for substrate selectivity, reaction mechanism and structure-based drug design. Chembiochem 2003, 4, 1066-1077.
70. Stengl, B.; Reuter, K.; Klebe, G. Mechanism and substrate specificity of tRNA-guanine transglycosylases (TGTs): tRNA-modifying enzymes from the three different kingdoms of life share a common catalytic mechanism. Chembiochem 2005, 6, 1926-1939.
71. Ritschel, T.; Atmanene, C.; Reuter, K.; van Dorsselaer, A.; Sanglier-Cianferani, S.; Klebe, G. An integrative approach combining noncovalent mass spectrometry, enzyme kinetics and X-ray crystallography to decipher Tgt protein-protein and protein-RNA interaction. J. Mol. Biol. 2009, 393, 833-847.
72. Vandenbergh, D.J.; Grant, M.D.; Severns, V. A simple tandem repeat polymorphism is present in the eighth intron of FLJ12960, a possible queuine salvage enzyme gene. Mol. Cell. Probes 2003, 17, 319-320.
73. Deshpande, K.L.; Seubert, P.H.; Tillman, D.M.; Farkas, W.R.; Katze, J.R. Cloning and characterization of cDNA encoding the rabbit tRNA-guanine transglycosylase 60-kilodalton subunit. Arch. Biochem. Biophys. 1996, 326, 1-7.
74. Ishiwata, S.; Ozawa, Y.; Katayama, J.; Kaneko, S.; Shindo, H.; Tomioka, Y.; Ishiwata, T.; Asano, G.; Ikegawa, S.; Mizugaki, M. Elevated expression level of 60-kDa subunit of tRNA-guanine transglycosylase in colon cancer. Cancer Lett. 2004, 212, 113-119.
75. Shinji, S.; Naito, Z.; Ishiwata, S.; Ishiwata, T.; Tanaka, N.; Furukawa, K.; Suzuki, H.; Seya, T.; Matsuda, A.; Katsuta, M.; et al. Ubiquitin-specific protease 14 expression in colorectal cancer is associated with liver and lymph node metastases. Oncol. Rep. 2006, 15, 539-543.
76. Morris, R.C.; Brooks, B.J.; Eriotou, P.; Kelly, D.F.; Sagar, S.; Hart, K.L.; Elliott, M.S. Activation of transfer RNA-guanine ribosyltransferase by protein kinase C. Nucleic Acids Res. 1995, 23, 2492-2498.
77. Reisser, T.; Langgut, W.; Kersten, H. The nutrient factor queuine protects HeLa cells from hypoxic stress and improves metabolic adaptation to oxygen availability. Eur. J. Biochem. 1994, 221, 979-986.
78. Langgut, W.; Reisser, T. Involvement of protein kinase C in the control of tRNA modification with queuine in HeLa cells. Nucleic Acids Res. 1995, 23, 2488-2491.
79. Szabo, L.; Nishimura, S.; Farkas, W.R. Possible involvement of queuine in oxidative metabolism. Biofactors 1988, 1, 241-244.
80. Marks, P.A.; Burka, E.R.; Schlessinger, D. Protein synthesis in erythroid cells, i. reticulocyte ribosomes active in stimulating amino acid incorporation. Proc. Natl. Acad. Sci. USA 1962, 48, 2163-2171.
81. Hankins, W.D.; Farkas, W.R. Guanylation of transfer RNA by rabbit reticulocytes. Biochim. Biophys. Acta 1970, 213, 77-89.
82. Farkas, W.R.; Singh, R.D. Guanylation of transfer ribonucleic acid by a cell-free lysate of rabbit reticulocytes. J. Biol. Chem. 1973, 248, 7780-7785.
83. Okada, N.; Harada, F.; Nishimura, S. Specific replacement of Q base in the anticodon of tRNA by guanine catalyzed by a cell-free extract of rabbit reticulocytes. Nucleic Acids Res. 1976, 3, 2593-2603.
84. Kung, F.L.; Garcia, G.A. tRNA-guanine transglycosylase from E. coli: Recognition of full-length 'queuine-cognate' tRNAs. FEBS Lett. 1998, 431, 427-432.
85. Curnow, A.W.; Garcia, G.A. tRNA-guanine transglycosylase from E. coli: Recognition of dimeric, unmodified tRNA (Tyr). Biochimie 1994, 76, 1183-1191.
86. Kung, F.L.; Nonekowski, S.; Garcia, G.A. tRNA-guanine transglycosylase from E. coli: Recognition of noncognate-cognate chimeric tRNA and discovery of a novel recognition site within the TpsiC arm of tRNA (Phe). RNA 2000, 6, 233-244.
87. Nonekowski, S.T.; Kung, F.L.; Garcia, G.A. The Escherichia coli tRNA-guanine transglycosylase can recognize and modify DNA. J. Biol. Chem. 2002, 277, 7178-7182.
88. Durand, J.M.; Okada, N.; Tobe, T.; Watarai, M.; Fukuda, I.; Suzuki, T.; Nakata, N.; Komatsu, K.; Yoshikawa, M.; Sasakawa, C. VacC, a virulence-associated chromosomal locus of Shigella flexneri, is homologous to tgt, a gene encoding tRNA-guanine transglycosylase (Tgt) of E. coli K-12. J. Bacteriol. 1994, 176, 4627-4634.
89. Hurt, J.K.; Olgen, S.; Garcia, G.A. Site-specific modification of Shigella flexneri virF mRNA by tRNA-guanine transglycosylase in vitro. Nucleic Acids Res. 2007, 35, 4905-4913.
90. Brooks, A.F.; Vélez-Martínez, C.S.; Showalter, H.D.; Garcia, G.A. Investigating the prevalence of queuine in E. coli RNA via incorporation of the tritium-labeled precursor, preQ(1). Biochem. Biophys. Res. Commun. 2012, 425, 83-88.
91. Haumont, E.; Droogmans, L.; Grosjean, H. Enzymatic formation of queuosine and of glycosyl queuosine in yeast tRNAs microinjected into Xenopus laevis oocytes. The effect of the anticodon loop sequence. Eur. J. Biochem. 1987, 168, 219-225.
92. Grosjean, H.; Edqvist, J.; Stråby, K.B.; Giegé, R. Enzymatic formation of modified nucleosides in tRNA: Dependence on tRNA architecture. J. Mol. Biol. 1996, 255, 67-85.
93. Phizicky, E.M.; Hopper, A.K. tRNA biology charges to the front. Genes Dev. 2010, 24, 1832-1860.
94. Carbon, P.; Haumont, E.; de Henau, S.; Keith, G.; Grosjean, H. Enzymatic replacement in vitro of the first anticodon base of yeast tRNAAsp: Application to the study of tRNA maturation in vivo, after microinjection into frog oocytes. Nucleic Acids Res. 1982, 10, 3715-3732.
95. Nishikura, K.; de Robertis, E.M. RNA processing in microinjected Xenopus oocytes. Sequential addition of base modifications in the spliced transfer RNA. J. Mol. Biol. 1981, 145, 405-420.
96. Krysko, D.V.; Agostinis, P.; Krysko, O.; Garg, A.D.; Bachert, C.; Lambrecht, B.N.; Vandenabeele, P. Emerging role of damage-associated molecular patterns derived from mitochondria in inflammation. Trends Immunol. 2011, 32, 157-164.
97. Green, D.R.; Galluzzi, L.; Kroemer, G. Mitochondria and the autophagy-inflammation-cell death axis in organismal aging. Science 2011, 333, 1109-1112.
98. Vafai, S.B.; Mootha, V.K. Mitochondrial disorders as windows into an ancient organelle. Nature 2012, 491, 374-383.
99. Itoh, K.; Nakamura, K.; Iijima, M.; Sesaki, H. Mitochondrial dynamics in neurodegeneration. Trends Cell. Biol. 2013, 23, 64-71.
100. Suzuki, T.; Nagao, A.; Suzuki, T. Human mitochondrial tRNAs: Biogenesis, function, structural aspects, and diseases. Annu. Rev. Genet. 2011, 45, 299-329.
101. Maniataki, E.; Mourelatos, Z. Human mitochondrial tRNAMet is exported to the cytoplasm and associates with the Argonaute 2 protein. RNA 2005, 11, 849-852.
102. Kolesnikova, O.A.; Entelis, N.S.; Mireau, H.; Fox, T.D.; Martin, R.P.; Tarassov, I.A. Suppression of mutations in mitochondrial DNA by tRNAs imported from the cytoplasm. Science 2000, 289, 1931-1933.
103. Rubio, M.A.; Rinehart, J.J.; Krett, B.; Duvezin-Caubet, S.; Reichert, A.S.; Söll, D.; Alfonzo, J.D. Mammalian mitochondria have the innate ability to import tRNAs by a mechanism distinct from protein import. Proc. Natl. Acad. Sci. USA 2008, 105, 9186-9191.
104. Okada, N.; Nishimura, S. Enzymatic synthesis of Q nucleoside containing mannose in the anticodon of tRNA: Isolation of a novel mannosyltransferase from a cell-free extract of rat liver. Nucleic Acids Res. 1977, 4, 2931-2938.
105. Farkas, W.R. Effect of diet on the queuosine family of tRNAs of germ-free mice. J. Biol. Chem. 1980, 255, 6832-6835.
106. Morris, R.C.; Brown, K.G.; Elliott, M.S. The effect of queuosine on tRNA structure and function. J. Biomol. Struct. Dyn. 1999, 16, 757-774.
107. Gündüz, U.; Katze, J.R. Salvage of the nucleic acid base queuine from queuine-containing tRNA by animal cells. Biochem. Biophys. Res. Commun. 1982, 109, 159-167.
108. Zallot, R.; Brochier-Armanet, C.; Gaston, K.W.; Forouhar, F.; Limbach, P.A.; Hunt, J.F.; de Crécy-Lagard, V. Plant, animal, and fungal micronutrient queuosine is salvaged by members of the DUF2419 protein family. ACS Chem. Biol. 2014, 9, 1812-1825.
109. Farkas, W.R. Queuine, the Q-containing tRNAs and the enzymes responsible for their formation. Nucleosides Nucleotides 1983, 2, 1-20.
110. Marks, T.; Farkas, W.R. Effects of a diet deficient in tyrosine and queuine on germfree mice. Biochem. Biophys. Res. Commun. 1997, 230, 233-237.
111. Shiman, R.; Gray, D.W. Formation and fate of tyrosine. Intracellular partitioning of newly synthesized tyrosine in mammalian liver. J. Biol. Chem. 1998, 273, 34760-34769.
112. Rakovich, T.; Boland, C.; Bernstein, I.; Chikwana, V.M.; Iwata-Reuyl, D.; Kelly, V.P. Queuosine deficiency in eukaryotes compromises tyrosine production through increased tetrahydrobiopterin oxidation. J. Biol. Chem. 2011, 286, 19354-19363.
113. Pathak, C.; Vinayak, M. Modulation of lactate dehydrogenase isozymes by modified base queuine. Mol. Biol. Rep. 2005, 32, 191-196.
114. Mahr, U.; Böhm, P.; Kersten, H. Possible involvement of queuine in control mechanisms of protein synthesis and protein phosphorylation in eukaryotes. Biofactors 1990, 2, 185-192.
115. Jacobson, K.B.; Farkas, W.R.; Katze, J.R. Presence of queuine in Drosophila melanogaster: correlation of free pool with queuosine content of tRNA and effect of mutations in pteridine metabolism. Nucleic Acids Res. 1981, 9, 2351-2366.
116. Eric Thomas, C.; Chen, Y.C.; Garcia, G.A. Differential heterocyclic substrate recognition by, and pteridine inhibition of E. coli and human tRNA-guanine transglycosylases. Biochem. Biophys. Res. Commun. 2011, 410, 34-39.
117. Parniak, M.A.; Andrejchyshyn, S.; Marx, S.; Kleiman, L. Alterations in cell tetrahydrobiopterin levels may regulate queuine hypomodification of tRNA during differentiation of murine erythroleukemia cells. Exp. Cell. Res. 1991, 195, 114-118.
118. Frazer, J.M.; Yang, W.K. Isoaccepting transfer ribonucleic acids in liver and brain of young and old BC3F 1 mice. Arch. Biochem. Biophys. 1972, 153, 610-618.
119. Shindo-Okada, N.; Terada, M.; Nishimura, S. Changes in amount of hypo-modified tRNA having guanine in place of queuine during erythroid differentiation of murine erythroleukemia cells. Eur. J. Biochem. 1981, 115, 423-428.
120. Lin, V.K.; Farkas, W.R.; Agris, P.F. Specific changes in Q-ribonucleoside containing transfer RNA species during Friend leukemia cell erythroid differentiation. Nucleic Acids Res. 1980, 8, 3481-3489.
121. Chen, Y.L.; Wu, R.T. Altered queuine modification of transfer RNA involved in the differentiation of human K562 erythroleukemia cells in the presence of distinct differentiation inducers. Cancer Res. 1994, 54, 2192-2198.
122. Schachner, E.; Aschhoff, H.J.; Kersten, H. Specific changes in lactate levels, lactate dehydrogenase patterns and cytochrome b559 in Dictyostelium discoideum caused by queuine. Eur. J. Biochem. 1984, 139, 481-487.
123. White, B.N.; Tener, G.M. Activity of a transfer RNA modifying enzyme during the development of Drosophila and its relationship to the su(s) locus. J. Mol. Biol. 1973, 74, 635-651.
124. Wosnick, M.A.; White, B.N. A doubtful relationship between tyrosine tRNA and suppression of the vermilion mutant in Drosophila. Nucleic Acids Res. 1977, 4, 3919-3930.
125. Owenby, R.K.; Stulberg, M.P.; Jacobson, K.B. Alteration of the Q family of transfer RNAs in adult Drosophila melanogaster as a function of age, nutrition, and genotype. Mech. Ageing Dev. 1979, 11, 91-103.
126. White, B.N.; Lassam, N.J. An analysis of Q and Q* containing tRNAs during the development of Lucilia sericata, Musca domestica and Tenebrio molitor. Insect Biochem. 1979, 9, 375-378.
127. Okada, N.; Shindo-Okada, N.; Sato, S.; Itoh, Y.H.; Oda, K.; Nishimura, S. Detection of unique tRNA species in tumor tissues by Escherichia coli guanine insertion enzyme. Proc. Natl. Acad. Sci. USA 1978, 75, 4247-4251.
128. Baranowski, W.; Dirheimer, G.; Jakowicki, J.A.; Keith, G. Deficiency of queuine, a highly modified purine base, in transfer RNAs from primary and metastatic ovarian malignant tumors in women. Cancer Res. 1994, 54, 4468-4471.
129. Aytaç, U.; Gündüz, U. Q-modification of tRNAs in human brain tumors. Cancer Biochem. Biophys. 1994, 14, 93-98.
130. Huang, B.S.; Wu, R.T.; Chien, K.Y. Relationship of the queuine content of transfer ribonucleic acids to histopathological grading and survival in human lung cancer. Cancer Res. 1992, 52, 4696-4700.
131. Emmerich, B.; Zubrod, E.; Weber, H.; Maubach, P.A.; Kersten, H.; Kersten, W. Relationship of queuine-lacking transfer RNA to the grade of malignancy in human leukemias and lymphomas. Cancer Res. 1985, 45, 4308-4314.
132. Singhal, R.P.; Vakharia, V.N. The role of queuine in the aminoacylation of mammalian aspartate transfer RNAs. Nucleic Acids Res. 1983, 11, 4257-4272.
133. Langgut, W.; Kersten, H. The deazaguanine-derivative, queuine, affects cell proliferation, protein phosphorylation and the expression of the proto oncogenes c-fos and c-myc in HeLa cells. FEBS 1990, 265, 33-36.
134. Langgut, W.; Reisser, T.; Nishimura, S.; Kersten, H. Modulation of mammalian cell proliferation by a modified tRNA base of bacterial origin. FEBS 1993, 336, 137-142.
135. Langgut, W.; Reisser, T.; Kersten, H. Queuine modulates growth of HeLa cells depending on oxygen availability. Biofactors 1990, 2, 245-249.
136. Morgan, C.J.; Merrill, F.L.; Trewyn, R.W. Defective transfer RNA-queuine modification in C3H10T1/2 murine fibroblasts transfected with oncogenic ras. Cancer Res. 1996, 56, 594-598.
137. Dubrul, E.F.; Farkas, W.R. Partial purification and properties of the reticulocyte guanylating enzyme. Biochim. Biophys. Acta 1976, 442, 379-390.
138. Jackson, C.D.; Irving, C.C.; Sells, B.H. Changes in rat liver transfer RNA following growth hormone administration and in regenerating liver. Biochim. Biophys. Acta 1970, 217, 64-71.
139. Borek, E.; Baliga, B.S.; Gehrke, C.W.; Kuo, C.W.; Belman, S.; Troll, W.; Waalkes, T.P. High turnover rate of transfer RNA in tumor tissue. Cancer Res. 1977, 37, 3362-3366.
140. Rokos, H.; Rokos, K.; Frisius, H.; Kirstaedter, H.J. Altered urinary excretion of pteridines in neoplastic disease. Determination of biopterin, neopterin, xanthopterin, and pterin. Clin. Chim. Acta 1980, 105, 275-286.
141. Katze, J.R.; Beck, W.T. Administration of queuine to mice relieves modified nucleoside queuosine deficiency in Ehrlich ascites tumor tRNA. Biochem. Biophys. Res. Commun. 1980, 96, 313-319.
142. Pathak, C.; Jaiswal, Y.K.; Vinayak, M. Hypomodification of transfer RNA in cancer with respect to queuosine. RNA Biol. 2005, 2, 143-148.
143. Pathak, C.; Jaiswal, Y.K.; Vinayak, M. Possible involvement of queuine inregulation of cell proliferation. BioFactors 2007, 29, 159-173.
144. Marini, M.; Mushinski, J.F. Transfer ribonucleic acids from eleven immunoglobulin-secreting mouse plasmacytomas. Constant and variable chromatographic profiles compared with the myeloma protein sequences. Biochim. Biophys. Acta 1979, 562, 252-270.
145. Yokoyama, S.; Miyazawa, T.; Iitaka, Y.; Yamaizumi, Z.; Kasai, H.; Nishimura, S. Three-dimensional structure of hyper-modified nucleoside Q located in the wobbling position of tRNA. Nature 1979, 282, 107-109.
146. McNamara, A.L.; Smith, D.W. The function of the histidine tRNA isoaccepting species in hemoglobin synthesis. J. Biol. Chem. 1978, 253, 5964-5970.
147. Meier, F.; Suter, B.; Grosjean, H.; Keith, G.; Kubli, E. Queuosine modification of the wobble base in tRNAHis infuences 'in vivo' decoding properties. EMBO J. 1985, 4, 823-827.
148. Novoa, E.M.; Ribas de Pouplana, L. Speeding with control: Codon usage, tRNAs, and ribosomes. Trends Genet. 2012, 28, 574-581.
149. Anderson, C.L.; Carew, E.A.; Powell, J.R. Evolution of the Adh locus in the Drosophila willistoni group: The loss of an intron, and shift in codon usage. Mol. Biol. Evol. 1993, 10, 605-618.
150. Powell, J.R.; Sezzi, E.; Moriyama, E.N.; Gleason, J.M.; Caccone, A. Analysis of a shift in codon usage in Drosophila. J. Mol. Evol. 2003, 57, S214-S225.
151. Vicario, S.; Moriyama, E.N.; Powell, J.R. Codon usage in twelve species of Drosophila. BMC Evol. Biol. 2007, 7, 226.
152. Moriyama, E.N.; Powell, J.R. Synonymous substitution rates in Drosophila: Mitochondrial versus nuclear genes. J. Mol. Evol. 1997, 45, 378-391.
153. Zaborske, J.M.; DuMont, V.L.; Wallace, E.W.; Pan, T.; Aquadro, C.F.; Drummond, D.A. A nutrient-driven tRNA modification alters translational fidelity and genome-wide protein coding across an animal genus. PLoS Biol. 2014, 12, e1002015.
154. Roth, A.; Winkler, W.C.; Regulski, E.E.; Lee, B.W.; Lim, J.; Jona, I.; Barrick, J.E.; Ritwik, A.; Kim, J.N.; Welz, R.; et al. A riboswitch selective for the queuosine precursor preQ1 contains an unusually small aptamer domain. Nat. Struct. Mol. Biol. 2007, 14, 308-317.
155. McCown, P.J.; Liang, J.J.; Weinberg, Z.; Breaker, R.R. Structural, functional, and taxonomic diversity of three preQ1 riboswitch classes. Chem. Biol. 2014, 21, 880-889.
156. Marchetti, M.; Capela, D.; Poincloux, R.; Benmeradi, N.; Auriac, M.C.; Le Ru, A.; Maridonneau-Parini, I.; Batut, J.; Masson-Boivin, C. Queuosine biosynthesis is required for sinorhizobium meliloti-induced cytoskeletal modifications on HeLa Cells and symbiosis with Medicago truncatula. PLoS ONE 2013, 8, e56043.
157. Ouzounis, C.A.; Kunin, V.; Darzentas, N.; Goldovsky, L. A minimal estimate for the gene content of the last universal common ancestor-exobiology from a terrestrial perspective. Res. Microbiol. 2006, 157, 57-68.