Abstract
SEPIAPTERIN and isosepiapterin are yellow, yellow -fluorescent compounds which occur in Drosophila melanogaster and accumulate in the sepia mutant. They are believed to be closely related 2-amino-4-oxo-6-acyltetrahydropteridines, the acyl group in isosepiapterin being propionyl and in sepiapterin, lactyl. However, there has been some controversy concerning the location of the hydrogen atoms on the pyrazine part of the molecule. Forrest1 favoured a distribution of the hydrogens on the 5 and 8 positions largely by analogy with the yellow 5,8-dihydro compounds (for example, I) synthesized by Pfleiderer and Taylor2, and with the 5,8-dihydro structure assigned to the red dihydroquinoxaline (II) on the basis of its nuclear magnetic resonance spectrum by Barltrop, Richards and Russell3.
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References
cf. Forrest, H. S., Abst. Seventeenth Intern. Congr. Pure and App. Chem., Munich, 1959, 2, 40 (1960).
Pfleiderer, W., and Taylor, E. C., J. Amer. Chem. Soc., 82, 3765 (1960).
Barltrop, J. A., Richards, C. G., and Russell, D. M., J. Chem. Soc., 1423 (1959).
Nawa, S., Bull. Chem. Soc. Japan, 33, 1555 (1960).
Kokka, J. P., Goldstein, J. H., and Mandell, L., J. Amer. Chem. Soc., 83, 2909 (1961).
Gatlin, L., and Davis, J. C., J. Amer. Chem. Soc. (in the press).
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FORREST, H., NAWA, S. Structures of Sepiapterin and Isosepiapterin. Nature 196, 372–373 (1962). https://doi.org/10.1038/196372b0
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DOI: https://doi.org/10.1038/196372b0
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