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Structure and Synthesis of Adenine Thiomethyl Pentoside; Synthesis of 5′-Methylthio Inosine

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Abstract

ADENINE thiomethyl pentoside is a sulphur-containing nucleoside first isolated from yeast1. On hydrolysis it yields adenine and a thio-pentose2 which was thought to be a ketose bearing a methylthio or methoxy substituent3 but later recognized as an aldose4. Periodate oxidation studies on the nucleoside, the thio-sugar, its osazone and the thio-pentitol obtained from it by reduction5,6, indicated a 5-methyl-thio group, while the positive Böeseken test for cis-1 : 2 glycols favoured the ribose configuration. The osazone of the thio-sugar was identical with that of 5-methylthio-d-arabinose; but the two sugars themselves were not identical6. The nucleoside must then be a derivative of 5-methylthio-d-ribose, and spectroscopic evidence favoured N9 for the position of attachment of sugar to purine7. The configuration about the glycosidic centre was unknown. On the basis of this evidence, formula (I) is considered probable for adenine thiomethyl pentoside.

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References

  1. Mandel and Dunham, J. Biol. Chem., 11, 85 (1912).

    CAS  Google Scholar 

  2. Suzuki, Ohdake and Mori, Biochem. Z., 154, 278 (1924).

    CAS  Google Scholar 

  3. Levene and Sobotka, J. Biol. Chem., 65, 551 (1925). Sobotka, ibid., 69, 267 (1926).

    CAS  Google Scholar 

  4. Wendt, Z. physiol. Chem., 272, 152 (1942).

    Article  CAS  Google Scholar 

  5. Satoh and Makino, Nature, 165, 769 (1950).

    Article  ADS  CAS  Google Scholar 

  6. Weygand, Trauth and Löwenfeld, Ber., 83, 563 (1950).

    CAS  Google Scholar 

  7. Falconer and Gulland, J. Chem. Soc., 1912 (1937).

  8. Levene and Tipson, J. Biol. Chem., 111, 313 (1935).

    CAS  Google Scholar 

  9. Kuhn and Henkel, Z. physiol. Chem., 269, 41 (1941).

    Article  CAS  Google Scholar 

  10. Suzuki, Ohdake and Mori, Biochem. Z., 162, 413 (1925).

    CAS  Google Scholar 

  11. Davoll, Lythgoe and Todd, J. Chem. Soc., 833 (1946); 967 (1948). Lythgoe, Smith and Todd, ibid., 355 (1947) inter al.

  12. Levene and Tipson, J. Biol. Chem., 121, 146 (1937).

    Google Scholar 

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Authors and Affiliations

  1. Lister Institute of Preventive Medicine, London, S.W.1

    J. BADDILEY

  2. Chemisches Institut der Universität, Heidelberg

    O. TRAUTH & F. WEYGAND

Authors
  1. J. BADDILEY
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  2. O. TRAUTH
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  3. F. WEYGAND
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BADDILEY, J., TRAUTH, O. & WEYGAND, F. Structure and Synthesis of Adenine Thiomethyl Pentoside; Synthesis of 5′-Methylthio Inosine. Nature 167, 359–360 (1951). https://doi.org/10.1038/167359b0

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