1887

Abstract

Summary: Cordycepin sensitive mutants of , which are permeable to 5'-deoxy-5'-methylthioadenosine (MTA), were used to study the fate of the methylthioribose carbons of this purine nucleoside. Evidence is presented for the recycling of the methylthio group and part of the ribose portion of MTA in a biosynthetic pathway which leads to the synthesis of methionine. The main pathway involves the phosphorylytic cleavage of MTA by MTA phosphorylase yielding 5-methylthioribose 1-phosphate and adenine as products. Loss of the phosphate group of 5-methylthioribose 1-phosphate, concurrent with the rearrangement of the ribose carbons, leads to the synthesis of 2-keto-4-methylthiobutyric acid. In the final step of the sequence, 2-keto-4-methylthiobutyric acid is converted to methionine via transamination. Several compounds not directly associated with the biosynthesis of methionine were also isolated. These compounds, which may arise through the degradation of intermediates in the pathway, were: 5'-methylthioinosine, a deaminated catabolite of MTA; 5-methylthioribose, a result of the phosphorylysis of 5-methylthioribose 1-phosphate, and 3-methylthiopropionaldehyde, 3-methylthiopropionic acid and 2-hydroxy-4-methylthiobutyric acid, all arising from the catabolism of 2-keto-4-methylthiobutyric acid.

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1985-09-01
2021-05-14
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References

  1. Anderson J. M., Roth R. M. 1974; Cordycepin sensitivity in adenosine utilizing mutants of S.cerevisiae. Biochimica et biophysica acta 335:285–289
    [Google Scholar]
  2. Backlund P. S., Smith R. A. 1981; Methionine synthesis from 5'-methylthioadenosine in rat liver. Journal of Biological Chemistry 256:1533–1535
    [Google Scholar]
  3. Backlund P. J., Chang C. P., Smith R. A. 1982; Identification of 2-keto-4-methylthiobutyrate as an intermediate compound in methionine synthesis from 5'-methylthioadenosine. Journal of Biological Chemistry 257:4196–4202
    [Google Scholar]
  4. Carteni-Farina M., Dellaragione F., Ragostar G., Oliva A., Zappia V. 1979; Studies on the metabolism of 5'-isobutylthioadenosine (SIBA). FEBS Letters 104:266–270
    [Google Scholar]
  5. Cohn M. S., Tabor C. W., Tabor H. 1977; Identification of a pyruvoyl residue in S-adenosyl-methionine decarboxylase from Saccharomyces cerevisiae. Journal of Biological Chemistry 252:8212–8216
    [Google Scholar]
  6. Cowwick S. P., Kaplan N. C. 1957; Procedure for the preparation of α-keto acids using L-amino acid oxidase. Methods in Enzymology 3:406–409
    [Google Scholar]
  7. Cone M. C., Marchitto K., Zehfus B., Ferro A.J. 1982; Role of 5'-methylthioadenosine in purine salvage in Saccharomyces cerevisiae. Journal of Bacteriology 151:510–515
    [Google Scholar]
  8. Cooper A. J. L., Meister A. 1974; Isolation and properties of a new glutamine transaminase from rat kidney. Journal of Biological Chemistry 249:2554–2561
    [Google Scholar]
  9. Dixon J. L., Benevenga N. J. 1980; The decarboxylation of α-keto-y-methiolbutyrate in rat liver mitochondria. Biochemical and Biophysical Research Communications 97:939–946
    [Google Scholar]
  10. Edwards C.H., Wade W. B., Freeburne M. M., Jones E.G., Stacey R. F., Sherman L., Seo C., Edwards G. A. 1977; Formation of methionine from α-amino-n-butyric acid and 5'-methylthioadenosine in the rat. Journalof Nutrition 107:1927–1936
    [Google Scholar]
  11. Everett G. B., Mitchell A. D., Benevenga N. J. 1979; Methionine transamination and catabolism in vitamin B-6 deficient rats. Journal of Nutrition 109:597–605
    [Google Scholar]
  12. Ferro A. J., Marchitto K. M. 1983; 5-Methylthioribose kinase: purification and properties of the enzyme from Enterobacter aerogenes. Methods in Enzymology 94:361–365
    [Google Scholar]
  13. Harter J. M., Baker D. H. 1977; Sulfur amino acid activity of glutathione, DL-α-hydroxy methionine, and α-keto-methionine in chicks. Proceedings of the Society for Experimental Biology and Medicine 156:201–204
    [Google Scholar]
  14. Hildesheim J., Hildesheim R., Lederer E. 1971; Synthesis of inhibitors of methyltransferases: analogs of S-adenosylhomocysteine. Biochimie 53:1067–1071
    [Google Scholar]
  15. Lawrence F., Richou M., Vedel M., Farrugia G., Blanchard P., Robert-Gero M. 1978; Identification of some metabolic products of 5'-deoxy-5'-S-isobutylthioadenosine, an inhibitor of virus-induced cell transformation. European Journal of Biochemistry 87:257–263
    [Google Scholar]
  16. Lawrence F., Chermann J.C., Robert-Gero M. 1980a; Metabolism of 5'-deoxy-5'[35S]-isobutylthio-adenosine (SIBA) in rats and mice. Biochemical Pharmacology 29:1963–1965
    [Google Scholar]
  17. Lawrence F., Richou M., Robert-Gero M. 1980b; Simultaneous decrease in deamination of 5'-adenylic acid and 5'-deoxy-5'-S-isobutylthioadeno sine in chick-embryo fibroblasts infected by Rous Sarcoma virus. European Journal of Biochemistry 107:467–473
    [Google Scholar]
  18. Matsui S., Amaha M. 1980; Gas chromatography analysis of medium and high-boiling sulfur volatiles in beer. Nippon Nogeikagaku Kaishi 54:629–636
    [Google Scholar]
  19. Matsui S., Ero M., Anaha M. 1980; Determination of methyl and ethyl mercaptans in lager beer. Nippon Nogeikuguku Kaishi 54:621–628
    [Google Scholar]
  20. Murr D. P., Yang S. F. 1975; Conversion of 5'methylthioadenosine to methionine by apple tissue. Phytochemistry 14:1291–1292
    [Google Scholar]
  21. Murray A. W. 1971; The biological significance of purine salvage. Annual Review of Biochemistry 40:811–826
    [Google Scholar]
  22. Robinson E. H., Allen O. W., Poe W. E., Wilson R. P. 1978; Utilization of dietary sulfur compounds by fingerling channel catfish: L-methionine, DL-methionine, methionine hydroxy analogue, taurine, and inorganic sulfate. Journal of Nutrition 108:1932–1936
    [Google Scholar]
  23. Ruiz-Herrera J., Starkey R. L. 1969; Dissimilation of methionine by fungi. Journal of Bacteriology 99:544–551
    [Google Scholar]
  24. Ruiz-Herrera J., Starkey R. L. 1970; Dissimilation of methionine by Achromobacter starkeyi. Journal of Bac1eriology 104:1286–1293
    [Google Scholar]
  25. Schlenk F. 1983; Methylthioadenosine. Advances in Enzymology 54:195–265
    [Google Scholar]
  26. Schlenk F., Ehninger D. J. 1964; Observations on the metabolism of 5'-methylthioadenosine. Archives of Biochemistry and Biophysics 106:95–100
    [Google Scholar]
  27. Schlenk F., Zydek-Cwick C.R., Hutson N. K. 1971; Enzymatic deamination of adenosine sulfur compounds. Archives of Biochemistry and Biophysics 142:144–149
    [Google Scholar]
  28. Scott J. H., Schekman R. 1980; Lyticase: endonuclease and protease activities that act together in cell lysis. Journal of Bacteriology 142:414–427
    [Google Scholar]
  29. Shapiro S.K., Barrett A. 1981; 5-Methylthioribose as a precursor of the carbon chain of methionine. Biochemical and Biophysical Research Communications 102:302–307
    [Google Scholar]
  30. Shapiro S. K., Schlenk F. 1980; Conversion of 5-methylthioadenosine into S-adenosylmethionine by yeast cells. Biochimica etbiophysica acta 633:176–180
    [Google Scholar]
  31. Steele R. D., Benevenga N. J. 1979; The synthesis of radioactive 3-methylthiopropionate and other alkylthio fatty acids. Analytical Biochemistry 98:281–286
    [Google Scholar]
  32. Sugimoto Y., Toraya T., Fukui s. 1976; Studies on metabolic role of 5'-methylthioadenosine inOchromonas malhamensis and other microorganisms. Archives of Microbiology 108:175–182
    [Google Scholar]
  33. Toohey J. I. 1977; Methylthio group cleavage from methylthioadenosine, description of an enzyme and its relationship to the methylthio requirement of certain cells in culture. Biochemical and Biophysical Research Communications 78:1273–1280
    [Google Scholar]
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