Riassunto
Viene descritta l'addizione fotochimica dei tioli al doppio legameeso della bilirubina. Si prospetta l'ipotesi che una reazione di questo tipo sia responsabile della rapida riduzione della bilirubinemia nei neonati itterici sottoposti a fototerapia.
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References
P. Manitto, Experientia27, 1147 (1971).
A. Hassner, J. org. Chem.33, 2684 (1968).
Irradiations were conducted as described in ref.1; thin-layer chromatography was carried out on polyamide [methanol −10% ammonia 9∶1 (v/v)], spraying the plates with diazotised sulphanilic acid in HCl dil.
All the new compounds blackened without melting over 250°; they gave correct elemental analyses consistent with the assigned structures.
Chemical shifts are in parts per million (δ) from internal tetramethylsilane;s, singlet;d, doublet;t, triplet;q, quartet;m, multiplet.
Partly buried beneath the signals of the central methylene bridge.
No isomer of IV, particularly V, was detected in the irradiation mixture.
C. K. Ingold,Structure and Mechanism in Organic Chemistry, 2nd ed. (Cornell University Press, Ithaca and London 1969), p. 451.
It was isolated from the irradiated solution made acid with HCl dil, and shown to be identical, by TLC, IR- and NMR-spectra, with compound VI obtained previously.
N. H. Martin, J. Am. chem. Soc.71, 1230 (1949). —D. Bratlid andJ. Fog, Scand. J. clin. Lab. Invest.25, 257 (1970) and references cited therein. —G. B. Odell, Pediatrics46, 16 (1970).
G. Franglen andG. R. E. Swaniker, Biochem. J.109, 107 (1968).
The authors wish to thank Prof.L. Canonica for helpful discussion and Dr.G. Severini Ricca for running NMR-spectra.
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Manitto, P., Monti, D. Photoaddition of sulphydryl groups to bilirubin in vitro. Experientia 28, 379–380 (1972). https://doi.org/10.1007/BF02008284
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DOI: https://doi.org/10.1007/BF02008284