Skip to main content
PMC home page
Biochemical Journal logoLink to Biochemical Journal
. 1989 Nov 1;263(3):635–640. doi: 10.1042/bj2630635

Biosynthesis and metabolism of 9-[5'-deoxy-5'-(methylthio)-beta-D-xylofuranosyl]adenine, a novel natural analogue of methylthioadenosine.

M Porcelli 1, G Cacciapuoti 1, G Cimino 1, M Gavagnin 1, G Sodano 1, V Zappia 1
PMCID: PMC1133480  PMID: 2512910

Abstract

The biosynthesis of 9-[5'-deoxy-5'-(methylthio)-beta-D-xylofuranosyl]adenine (xylosyl-MTA), a naturally occurring analogue of 5'-deoxy-5'-methylthioadenosine (MTA) recently characterized, was studied in the nudibranch mollusc Doris verrucosa. Experiments performed in vivo with putative labelled precursors such as [8-14C]adenine, [Me-14C]methionine and [Me-14C]MTA indicate that xylosyl-MTA originates from MTA. Experiments with MTA double-labelled at critical positions are consistent with a 3'-isomerization of the nucleoside through the formation of a 3'-oxo intermediate. In addition, experiments with the newly synthesized [3'-3H]xylosyl-MTA are indicative for a very low turnover rate of this molecule, which therefore accumulates in the mollusc.

Full text

PDF
638

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Bradford M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976 May 7;72:248–254. doi: 10.1006/abio.1976.9999. [DOI] [PubMed] [Google Scholar]
  2. Cacciapuoti G., Oliva A., Zappia V. Studies on phosphate-activated 5'-methylthioadenosine nucleosidase from human placenta. Int J Biochem. 1978;9(1):35–41. doi: 10.1016/0020-711x(78)90135-0. [DOI] [PubMed] [Google Scholar]
  3. Della Ragione F., Cartenì-Farina M., Gragnaniello V., Schettino M. I., Zappia V. Purification and characterization of 5'-deoxy-5'-methylthioadenosine phosphorylase from human placenta. J Biol Chem. 1986 Sep 15;261(26):12324–12329. [PubMed] [Google Scholar]
  4. Della Ragione F., Cartenì-Farina M., Porcelli M., Cacciapuoti G., Zappia V. High-performance liquid chromatographic analysis of 5'-methylthioadenosine in rat tissues. J Chromatogr. 1981 Nov 13;226(1):243–249. doi: 10.1016/s0378-4347(00)84229-2. [DOI] [PubMed] [Google Scholar]
  5. Di Fiore P. P., Grieco M., Pinto A., Attadia V., Porcelli M., Cacciapuoti G., Cartenì-Farina M. Inhibition of dimethyl sulfoxide-induced differentiation of Friend erythroleukemic cells by 5'-methylthioadenosine. Cancer Res. 1984 Sep;44(9):4096–4103. [PubMed] [Google Scholar]
  6. Hibasami H., Hoffman J. L., Pegg A. E. Decarboxylated S-adenosylmethionine in mammalian cells. J Biol Chem. 1980 Jul 25;255(14):6675–6678. [PubMed] [Google Scholar]
  7. Pajula R. L., Raina A. Methylthioadenosine, a potent inhibitor of spermine synthase from bovine brain. FEBS Lett. 1979 Mar 15;99(2):343–345. doi: 10.1016/0014-5793(79)80988-6. [DOI] [PubMed] [Google Scholar]
  8. Pegg A. E., Borchardt R. T., Coward J. K. Effects of inhibitors of spermidine and spermine synthesis on polyamine concentrations and growth of transformed mouse fibroblasts. Biochem J. 1981 Jan 15;194(1):79–89. doi: 10.1042/bj1940079. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Porcelli M., Cacciapuoti G., Cartení-Farina M., Gambacorta A. S-adenosylmethionine synthetase in the thermophilic archaebacterium Sulfolobus solfataricus. Purification and characterization of two isoforms. Eur J Biochem. 1988 Nov 1;177(2):273–280. doi: 10.1111/j.1432-1033.1988.tb14373.x. [DOI] [PubMed] [Google Scholar]
  10. Porcelli M., Cacciapuoti G., Oliva A., Zappia V. High-performance liquid chromatographic determination of a naturally occurring xylosyl thioether, 9-[5'-deoxy-5'(methylthio)-beta-D-xylofuranosyl]adenine. J Chromatogr. 1988 May 25;440:151–155. doi: 10.1016/s0021-9673(00)94519-9. [DOI] [PubMed] [Google Scholar]
  11. Raina A., Eloranta T., Pajula R. L. Rapid assays for putrescine aminopropyltransferase (spermidine synthase) and spermidine aminopropyltransferase (spermine synthase). Methods Enzymol. 1983;94:257–260. doi: 10.1016/s0076-6879(83)94044-2. [DOI] [PubMed] [Google Scholar]
  12. SCHLENK F., DEPALMA R. E. The formation of S-adenosylmethionine in yeast. J Biol Chem. 1957 Dec;229(2):1037–1050. [PubMed] [Google Scholar]
  13. SCHLENK F., EHNINGER D. J. OBSERVATIONS ON THE METABOLISM OF 5'-METHYLTHIOADENOSINE. Arch Biochem Biophys. 1964 Jul 20;106:95–100. doi: 10.1016/0003-9861(64)90161-4. [DOI] [PubMed] [Google Scholar]
  14. Shapiro S. K., Ehninger D. J. Methods for the analysis and preparation of adenosylmethionine and adenosylhomocysteine. Anal Biochem. 1966 May;15(2):323–333. doi: 10.1016/0003-2697(66)90038-8. [DOI] [PubMed] [Google Scholar]
  15. Wickner R. B., Tabor C. W., Tabor H. Purification of adenosylmethionine decarboxylase from Escherichia coli W: evidence for covalently bound pyruvate. J Biol Chem. 1970 Apr 25;245(8):2132–2139. [PubMed] [Google Scholar]
  16. Williams-Ashman H. G., Seidenfeld J., Galletti P. Trends in the biochemical pharmacology of 5'-deoxy-5'-methylthioadenosine. Biochem Pharmacol. 1982 Feb 1;31(3):277–288. doi: 10.1016/0006-2952(82)90171-x. [DOI] [PubMed] [Google Scholar]
  17. Zappia V., Cartenì-Farina M., Galletti P., Della Ragione F., Cacciapuoti G. High-performance liquid chromatographic analysis of adenosyl-sulfur compounds related to polyamine biosynthesis. Methods Enzymol. 1983;94:57–66. doi: 10.1016/s0076-6879(83)94010-7. [DOI] [PubMed] [Google Scholar]
  18. Zappia V., Galletti P., Porcelli M., Manna C., Ragione F. D. High-performance liquid chromatographic separation of natural adenosyl-sulphur compounds. J Chromatogr. 1980 Mar 7;189(3):399–405. doi: 10.1016/s0021-9673(00)80319-2. [DOI] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES