Abstract
4-AMINO-5-hydroxymethyl-2-methylthiopyrim-idine1,2 (I) is an inhibitory antagonist of the pyrimidine moiety of vitamin B1 (II)3. However, a thiamine-requiring mutant of Escherichia coli (strain M70–17) which can use II for growth will grow in the presence of I if the thiazole moiety of thiamine is also supplied. One possible explanation of this is that, under these conditions, the pyrimidine I is being converted to a functional thiamine-like compound. Consequently, it was decided to synthesize the thiamine analogue derived from I, which would differ from thiamine only in the nature of the 2-substituent, and 
which, on the basis of a recently proposed mechanism of thiamine action4, might be expected to have thiamine activity.
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References
Ulbricht, T. L. V., and Price, C. C., Chem. and Indust., 1221 (1955). (erratum, Chem. and Indust., 290 (1956)).
Ulbricht, T. L. V., and Price, C. C., J. Org. Chem., 21, 567 (1956).
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See, for example, Dornow, A., and Petsch, G., Ann., 588, 45 (1954).
Dornow, A. (private communication to Ulbricht, T. L. V.).
vide, for example, Makino, K., Kinoshita, T., Aramaki, Y., and Shintani, S., Nature, 174, 275 (1954). Harris, D. L., Arch. Biochem. Biophys., 60, 35 (1956).
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ULBRICHT, T., GOTS, J. A New Antagonist of Thiamine. Nature 178, 913–914 (1956). https://doi.org/10.1038/178913a0
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DOI: https://doi.org/10.1038/178913a0
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