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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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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DOI: https://doi.org/10.1038/167359b0
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