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Structure of Adenylthiomethylpentose

Abstract

ACCORDING to Nakahara et al.1, adenylthiomethylpentose has the same effect as vitamin L2 (L1 is said to be anthranilic acid). Adenylthiomethylpentose was isolated from yeast2, from crude oryzanine3, and from impure cozymase4, and yielded adenine and thiosugar on acid hydrolysis. Falconer and Gulland5 state that the thiosugar is combined to the 9-position of the adenine. The thiosugar itself has been the subject of several studies: according to Suzuki, Ohdake and Mori3,6, the thiosugar gives the Molisch test with all other reducing sugar tests, and strong pentose reactions, but gives neither the methylpentose reaction nor Seliwanoff's. The sulphur can be detected only after fusion of the thiosugar with metallic sodium; and by estimation of the thiomethyl group, the Japanese authors assigned to the sugar the structure of 5-thiomethylpentose, and showed that the sugar could be reduced by means of sodium amalgam to the thiomethyl group containing polyalcohol (thiopentitol) (I).

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References

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SATOH, K., MAKINO, K. Structure of Adenylthiomethylpentose. Nature 165, 769–770 (1950). https://doi.org/10.1038/165769a0

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