Synthesis of dinucleoside polyphosphates catalyzed by firefly luciferase and several ligases

Pharmacology and Therapeutics

Volumn 87, Issue 2-3, 2000, Pages 91-102

  Sillero, Antonio ^a   Sillero, María Antonia Günther ^a  

^a INSTITUTO DE INVESTIGACIONES BIOMÉDICAS ALBERTO SOLS   (Spain)

Author keywords

Acetyl CoA synthetase; Acyl CoA synthetase; Diadenosine tetraphosphate; Dinucleoside polyphosphates; T4 DNA ligase; T4 RNA ligase

Indexed keywords

ACETYL COENZYME A SYNTHETASE; ADENOSINE TRIPHOSPHATE; DIADENOSINE POLYPHOSPHATE; DIADENOSINE TETRAPHOSPHATE; DINUCLEOSIDE PHOSPHATE; DOUBLE STRANDED DNA; LIGASE; LONG CHAIN FATTY ACID COENZYME A LIGASE; LUCIFERASE; NUCLEOSIDE DERIVATIVE; NUCLEOSIDE TRIPHOSPHATE; OXIDOREDUCTASE; PHOSPHATE; POLYDEOXYRIBONUCLEOTIDE SYNTHASE; PYROPHOSPHATE; RNA DIRECTED DNA POLYMERASE; RNA LIGASE;

CATALYSIS; COMPLEX FORMATION; CONFERENCE PAPER; DNA STRAND BREAKAGE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SPECIFICITY; HUMAN IMMUNODEFICIENCY VIRUS 1; LIGASE CHAIN REACTION; LIGATION; NONHUMAN; PRIORITY JOURNAL; PURINE SYNTHESIS;

ACETATE-COA LIGASE; ANIMAL; COENZYME A LIGASES; DINUCLEOSIDE PHOSPHATES; DNA LIGASES; KINETICS; LUCIFERINS; RNA-DIRECTED DNA POLYMERASE; SUPPORT, NON-U.S. GOV'T;

EID: 0033796867     PISSN: 01637258     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0163-7258(00)00047-4     Document Type: Conference Paper

References (72)

1. Airth R.L., Rhodes W.C., McElroy W.D. The function of coenzyme A in luminescence. Biochim Biophys Acta. 27:1958;519-532.
2. Armstrong J., Brown R.S., Tsugita A. Primary structure and genetic organization of phage T4 DNA ligase. Nucleic Acids Res. 11:1983;7145-7156.
3. Atencia E.A., Madrid O., Günther Sillero M.A., Sillero A. T4 RNA ligase catalyzes the synthesis of dinucleoside polyphosphates. Eur J Biochem. 261:1999;802-811.
4. Bar-Tana J., Rose G., Brandes R., Shapiro B. Palmitoyl-coenzyme A synthetase. Mechanism of reaction. Biochem J. 131:1973;199-209. a.
5. Bar-Tana J., Rose G., Shapiro B. Palmitoyl-coenzyme A synthetase. Isolation of an enzyme bound intermediate. Biochem J. 135:1973;411-416. b.
6. Berg P. Acyl adenylates. an enzymatic mechanism of acetate activation J Biol Chem. 222:1956;991-1013.
7. Bernet D., Pinto R.M., Sillero A., Cameselle J.C. Location of dinucleoside triphosphatase in the matrix space of rat liver mitochondria. FEBS Lett. 283:1991;286-288.
8. Bremer J., Osmundsen H. Fatty acid oxidation and its regulation. Numa S. Fatty Acid Metabolism and Its Regulation. 1984;113-154 Elsevier Science Publishers, Amsterdam.
9. Brennan C.A., Manthey A.E., Gumport R.I. Using T4 RNA ligase with DNA substrates. Methods Enzymol. 100:1983;38-52.
10. 4A and other dinucleoside polyphosphates in stressed Drosophila cells. J Biol Chem. 260:1985;15566-15570.
11. Cartwright J.L., McLennan A.G. Formation of a covalent Nepsilon2-guanylylhistidyl reaction intermediate by the GTP:GTP guanylyltransferase from the brine shrimp Artemia. Arch Biochem Biophys. 361:1999;101-105.
12. Chang K.H., Xiang H., Dunaway-Mariano D. Acyl-adenylate motif of the acyl-adenylate/thioester-forming enzyme superfamily. a site-directed mutagenesis study with the Pseudomonas sp. strain CBS3 4-chlorobenzoate: coenzyme A ligase Biochemistry. 36:1997;15650-15659.
13. Connolly K.J., Hammer S.M. Antiretroviral therapy. reverse transcriptase inhibition Antimicrob Agents Chemother. 36:1992;245-254.
14. Conti E., Franks N.P., Brick P. Crystal structure of firefly luciferase throws light on a superfamily of adenylate-forming enzymes. Structure. 4:1996;287-298.
15. Costas M.J., Cameselle J.C., Sillero A. Mitochondrial location of rat liver dinucleoside triphosphatase. J Biol Chem. 261:1986;2064-2067.
16. Cranston J.W., Silber R., Malathi V.G., Hurwitz J. Studies on ribonucleic acid ligase. Characterization of an adenosine triphosphate-inorganic pyrophosphate exchange reaction and demonstration of an enzyme-adenylate complex with T4 bacteriophage-induced enzyme. J Biol Chem. 249:1974;7447-7456.
17. DeLuca M. Firefly luciferase. Adv Enzymol. 44:1976;37-68.
18. DeLuca M., McElroy W.D. Two kinetically distinguishable ATP sites in firefly luciferase. Biochem Biophys Res Commun. 123:1984;764-770.
19. DeLuca M., Wannlund J., McElroy W.D. Factors affecting the kinetics of light emission from crude and purified firefly luciferase. Anal Biochem. 95:1979;194-198.
20. Denburg J.L., Reiko T.L., McElroy W.D. Substrate-binding properties of firefly luciferase. I. Luciferin-binding site. Arch Biochem Biophys. 134:1969;381-394.
21. Dukhovich A., Sillero A., Günther Sillero M.A. Time course of luciferyl adenylate synthesis in the firefly luciferase reaction. FEBS Lett. 395:1996;188-190.
22. Engler M.J., Richardson C.C. DNA ligases. Boyer P.D. The Enzymes, 3rd edn., Vol. XV. 1982;3-29 Academic Press, New York.
23. Fontes R., Dukhovich A., Sillero A., Günther Sillero M.A. Synthesis of dehydroluciferin by firefly luciferase. effect of dehydroluciferin, coenzyme A and nucleosides triphosphates on the luminescent reaction Biochem Biophys Res Commun. 237:1997;445-450.
24. Fontes R., Günther Sillero M.A., Sillero A. Acyl coenzyme A synthetase from Pseudomonas fragi catalyzes the synthesis of adenosine 5′-polyphosphates and dinucleoside polyphosphates. J Bacteriol. 180:1998;3152-3158. a.
25. 4A catalyzed by firefly luciferase. FEBS Lett. 438:1998;190-194. b.
26. 6A). Biochimie. 81:1999;1-6.
27. Frenkel E.P., Kitchens R.L. Purification and properties of acetyl coenzyme A synthetase from bakers' yeast. J Biol Chem. 252:1977;504-507.
28. 4N). Synthesis with firefly luciferase. J Biochem Biophys Methods. 30:1995;191-198.
29. Goto T., Kubota I., Suzuki N., Kishi Y. Aspects of the mechanism of bioluminescence. Cormier M.J., Hercules D.M., Lee J. Chemiluminescence and Bioluminescence. 1974;325-335 Plenum, New York.
30. Groot P.H.E., Van Loon C.M.I., Hülsmann W.C. Identification of the palmitoyl-CoA synthetase in the inner membrane-matrix fraction of rat liver mitochondria. Biochim Biophys Acta. 337:1974;1-12.
31. Guranowski A. Specific and nonspecific enzymes involved in the catabolism of mononucleoside and dinucleoside polyphosphates. Pharmacol Ther. 87(2-3):2000;117-139.
32. 4A and Other Dinucleoside Polyphosphates. 1992;81-133 CRC Press, Inc, Boca Raton.
33. 4A) and other dinucleoside polyphosphates. FEBS Lett. 271:1990;215-218.
34. Guranowski A., Günther Sillero M.A., Sillero A. Adenosine 5′-tetraphosphate and adenosine 5′-pentaphosphate are synthesized by acetyl coenzyme A synthetase. J Bacteriol. 176:1994;2986-2990.
35. Harnett S.P., Lowe G., Tansley G. A stereochemical study of the mechanism of activation of donor oligonucleotides by RNA ligase from bacteriophage T4 infected Escherichia coli. Biochemistry. 24:1985;7446-7449.
36. Hastings J.W., McElroy W.D., Coulombre J. The effect of oxygen upon the immobilization reaction in firefly luminescence. J Cell Comp Physiol. 42:1953;137-150.
37. Hesler C.B., Olymbios C., Haldar D. Transverse-plane topography of long-chain acyl-CoA synthetase in the mitochondrial outer membrane. J Biol Chem. 265:1990;6600-6605.
38. 4-tetraphosphate by organellar and cytoplasmic phenylalanyl-tRNA synthetases of Euglena gracilis. FEBS Lett. 235:1988;275-277.
39. Lembert N., Idahl L.-A. Regulatory effects of ATP and luciferin on firefly luciferase activity. Biochem J. 305:1995;929-933.
40. Lindahl T., Barnes D.E. Mammalian DNA ligases. Annu Rev Biochem. 61:1992;251-281.
41. Liu J.J., McLennan A.G. Purification and properties of GTP:GTP guanylyltransferase from encysted embryos of the brine shrimp. Artemia. J Biol Chem. 269:1994;11787-11794.
42. Madrid O., Martín D., Atencia E.A., Sillero A., Günther Sillero M.A. T4 DNA ligase synthesizes dinucleoside polyphosphates. FEBS Lett. 433:1998;283-286.
43. Marques A.F.P., Teixeira N.A., Gambaretto C., Sillero A., Günther Sillero M.A. IMP-GMP 5′-nucleotidase from rat brain. activation by polyphosphates J Neurochem. 71:1998;1241-1250.
44. McElroy W.D., DeLuca M., Travis J. Molecular uniformity in biological catalyses. Science. 157:1967;150-160.
45. McElroy W.D., Seliger H.H., White E.H. Mechanism of bioluminescence, chemiluminescence and enzyme function in the oxidation of firefly luciferin. Photochem Photobiol. 10:1969;153-170.
46. Meyer P.R., Matsuura S.E., So A.G., Scott W.A. Unblocking of chain-terminated primer by HIV-1 reverse transcriptase through a nucleotide-dependent mechanism. Proc Natl Acad Sci USA. 95:1998;13471-13476.
47. Miyazawa S., Hashimoto T., Yokota S. Identity of long-chain acyl-coenzyme A synthetase of microsomes, mitochondria, and peroxisomes in rat liver. J Biochem (Tokyo). 98:1985;723-733.
48. 5-di(adenosine-5′-) pentaphosphate and adenosine-5′-tetraphosphate. Biochem Biophys Res Commun. 84:1978;816-822.
49. 4A) levels in subpicomole quantities by a phosphodiesterase luciferin-luciferase coupled assay. application as a specific assay for diadenosine tetraphosphatase Anal Biochem. 115:1981;302-307.
50. Orr D.C., Figueiredo H.T., Mo Ch.-L., Penn C.R., Cameron J.M. DNA chain termination activity and inhibition of human immunodeficiency virus reverse transcriptase by carbocyclic 2′,3′-didehydro-2′,3′-dideoxyguanosine triphosphate. J Biol Chem. 267:1992;4177-4182.
51. Ortiz B., Sillero A., Günther Sillero M.A. Specific synthesis of adenosine(5′)tetraphospho(5′)nucleoside and adenosine(5′)oliphospho(5′)adenosine (n > 4) catalyzed by firefly luciferase. Eur J Biochem. 212:1993;263-270.
52. 4A) by firefly luciferase. J Photochem Photobiol B. 29:1995;33-36.
53. Philipp D.P., Parsons P. Kinetic characterization of long chain fatty acyl coenzyme A ligase from rat liver mitochondria. J Biol Chem. 254:1979;10785-10790.
54. 4A and Other Dinucleoside Polyphosphates. 1992;63-79 CRC Press, Inc, Boca Raton.
55. Randerath K., Janeway C.M., Stephenson M.L., Zamecnik P.C. Isolation and characterization of dinucleoside tetra- and tri-phosphates formed in the presence of lysyl-tRNA synthetase. Biochem Biophys Res Commun. 24:1966;98-105.
56. 4-tetraphosphate, and immunological relationship of phenylalanyl-tRNA synthetases from different urkingdoms. J Biol Chem. 260:1985;182-187.
57. Rhodes W.C., McElroy W.D. Enzymatic synthesis of adenyl-oxyluciferin. Science. 128:1958;253-254. a.
58. Rhodes W.C., McElroy W.D. The synthesis and function of luciferyl-adenylate and oxyluciferyl-adenylate. J Biol Chem. 233:1958;1528-1537. b.
59. Romaniuk P.J., Uhlenbeck O.C. Joining of RNA molecules with RNA ligase. Methods Enzymol. 100:1983;52-59.
60. Rose G., Bar-Tana J., Shapiro B. Palmitoyl coenzyme A synthetase activation by uncomplexed ATP. Biochim Biophys Acta. 573:1979;126-135.
61. Sillero A., Günther Sillero M.A. Purine nucleotide metabolism in Artemia. MacRae T., Bagshaw J.C., Warner A.H. Biochemistry and Cell Biology of Artemia. 1989;289-307 CRC Press, Inc, Boca Raton.
62. Sillero M.A.G., Guranowski A., Sillero A. Synthesis of dinucleoside polyphosphates catalyzed by firefly luciferase. Eur J Biochem. 202:1991;507-513.
63. 4N counterparts as substrates of firefly luciferase, dinucleoside tetraphosphatase and phosphodiesterases. Biochim Biophys Acta. 1334:1997;191-199.
64. Singh H., Poulos A. Distinct long chain and very long chain fatty acyl CoA synthetases in rat liver peroxisomes and microsomes. Arch Biochem Biophys. 266:1988;486-495.
65. Suzuki N., Goto T. Studies on firefly bioluminescence. II. Identification of oxyluciferin as a product in the bioluminescence of firefly lanterns and in the chemiluminescence of firefly luciferin. Tetrahedron. 28:1972;4075-4081.
66. Tessier D.C., Brousseau R., Vernet T. Ligation of single-stranded oligodeoxyribonucleotides by T4 RNA ligase. Anal Biochem. 158:1986;171-178.
67. Uhlenbeck O.C., Gumport R.I. T4 RNA ligase. Boyer P.D. The Enzymes, 3rd edn., Vol. XV. 1982;31-58 Academic Press, New York.
68. 4A and Other Dinucleoside Polyphosphates. 1992;275-303 CRC Press, Inc, Boca Raton.
69. White E.L., Parker W.B., Ross L.J., Shannon W.M. Lack of synergy in the inhibition of HIV-1 reverse transcriptase by combinations of the 5′-triphosphates of various anti-HIV nucleoside analogs. Antiviral Res. 22:1993;295-308.
70. Wood K.V. The chemical mechanism and evolutionary development of beetle bioluminescence. Photochem Photobiol. 62:1995;662-673.
71. Zamecnik P.C., Stephenson M.L. A possible regulatory site located at the gateway to protein synthesis. San Pietro A., Lamborg M.R., Kenney F.T. Regulatory Mechanisms for Protein Synthesis in Mammalian Cells. 1968;3-16 Academic Press, Inc, New York.
72. Zamecnik P.C., Stephenson M.L., Janeway C.M., Randerath K. Enzymatic synthesis of diadenosine tetraphosphate and diadenosine triphosphate with purified lysyl-tRNA synthetase. Biochem Biophys Res Commun. 24:1966;91-97.