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Natural Pteridines -A Chemical Hobby

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Chemistry and Biology of Pteridines and Folates

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 338))

Abstract

The natural pteridines can be regarded as the origin of pteridine chemistry in general and have initiated and stimulated research in this field to a very large extent ever since Frederick Gowland Hopkins has focussed for the first time more than 100 years ago1 the attention to butterfly pigments in trying to isolate the yellow pigments from the English brimstone butterfly and the white pigment from the cabbage butterfly six years later2. The unusual physical and chemical properties of these substances, however, did not allow to get pure materials suitable for structure elucidations. From 1924 – 1926 Clemens Schöpf3,4 took up Hopkins’ observations in Heinrich Wieland’s laboratory and named the pigments according to their colors and appearance in nature xanthopterin (2) and leucopterin (4). In 1933 a third component, isoxanthopterin (3)5, was isolated, but his constitution remained also unknown until Robert Purrmann was able to elucidate the structures of all three pigments6–8, which turned out to be derivatives of the pyrazine [2,3-d]pyrimidine (1) ringsystem termed by Wieland9 pteridine.

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References

  1. F.G.Hopkins, Note on a yellow pigment in butterflies, Proc.Chem.Soc. 5: 117, (1889).

    Google Scholar 

  2. F.G.Hopkins, Über den gelben Farbstoff bei Schmetterlingen, Ber.Deut.Chem. Ges. 24: 724 (1891),.

    Google Scholar 

  3. F.G.Hopkins, Note on yellow Pigments in Butterflies (Note), Nature, (London) 40: 335 (1889).

    Article  Google Scholar 

  4. F.G. Hopkins, The pigments of the piedidae: a contribution to the study of excretory substances which function in ornament, Philos.Trans.Roy.Soc. London, Ser. B,186: 661 (1895).

    Article  Google Scholar 

  5. H. Wieland and CI. Schöpf, Über den gelben Flügelfarbstoff des Citronenfalters (Gonepteryx rhamni), Ber.Deut.Chem.Ges. 58: 2178 (1925).

    Article  Google Scholar 

  6. CI. Schöpf and H. Wieland, Über das Leukopterin, das weiße Flügelpigment der Kohlweißlinge (Pieris brassicae und P. napi), Ber.Deut.Chem.Ges. 59: 2067 (1926).

    Article  Google Scholar 

  7. H. Wieland, H. Metzger, CI. Schöpf and M. Billow, Leukopterin, das Flügelpigment der Kohlweißlinge, Liebigs Ann.Chem. 507: 261 (1933).

    Google Scholar 

  8. R. Purrmann, Über die Flügelpigmente der Schmetterlinge. VII Synthese des Leukopterins und Natur des Guanopterins, Liebigs Ann.Chem. 544: 182 (1940).

    Article  CAS  Google Scholar 

  9. R. Purrmann, Über die Flügelpigmente der Schmetterlinge. X Die Synthese des Xanthopterins, Liebigs Ann.Chem. 546: 98 (1940).

    CAS  Google Scholar 

  10. R. Purrmann, Über die Flügelpigmente der Schmetterlinge. XII Konstitution und Synthese des sogenannten Anhydroleukopterins, Liebigs Ann.Chem. 548: 284 (1941).

    Article  CAS  Google Scholar 

  11. CI. Schöpf, R.Reichert und K. Riefstahl, Zur Kenntnis des Leukopterins, Liebigs Ann.Chem. 548: 82 (1941).

    Article  Google Scholar 

  12. CI. Schöpf and E. Becker, Über neue Pterine, Liebigs Ann.Chem. 524: 49 (1936).

    Article  Google Scholar 

  13. R. Purrmann and F. Eulitz, Über die Flügelpigmente der Schmetterlinge. XVI Zur Kenntnis des Erythropterins, Liebigs Ann.Chem. 559: 169 (1949).

    Google Scholar 

  14. R. Tschesche and F. Korte, Die Synthese des Erythropterins, Chem.Ber. 84: 77 (1951).

    Article  CAS  Google Scholar 

  15. W. Pfleiderer, Isolierung und Struktur des orangeroten Schmetterlingspigmentes“Erythropterin”, Chem.Ber. 95: 2195 (1962).

    Article  CAS  Google Scholar 

  16. W. von Philipsborn, H. Stierlin, and W. Traber, Zur Struktur von 9-Acetonylxanthopterin und Erythropterin, Helv.Chim. Acta 46: 2592 (1963).

    Article  CAS  Google Scholar 

  17. W. Pfleiderer, Pterorhodin, ein neues natürliches Schmetterlingspigment, Z. Naturforsch. 14b: 654 (1963).

    Google Scholar 

  18. F.G. Hopkins, A contribution to the chemistry of pterins, Proc.Roy.Soc. London (B), 130: 359 (1942).

    Article  CAS  Google Scholar 

  19. R. Purrmann and M. Maas, Zur Kenntnis des Pterorhodins, Liebigs Ann.Chem. 556:186 (1944).

    Article  CAS  Google Scholar 

  20. P.B. Russell, R. Purrmann, W. Schmitt and G.H. Hitchings, The Synthesis of Pterorhodin (Rhodopterin), J.Am.Chem.Soc. 71: 3412 (1949).

    Article  CAS  Google Scholar 

  21. A. Kühn and A. Egelhaf, Der rote Augenfarbstoff von Ephestia und Ptychopoda-ein Pterinpigment, Z. Naturforsch. 14b: 654 (1959).

    Google Scholar 

  22. M. Viscontini, W. Hummel and A.Fischer, Isolierung von Pterindimeren aus den Augen von Platynereis dummerilli 1833, Helv.Chim. Acta 53: 1207 (1970).

    CAS  Google Scholar 

  23. G. Misuraca, G. Prota, J.T. Bagnara and S.K. Frost, Identification of the leaffrog melanophore pigment, Rhodomelanochrome, as pterorhodin, Comp. Biochem.Physiol. 57B: 41 (1977).

    Google Scholar 

  24. W. Pfleiderer, Über 7-Hydroxy-und 7-Hydroxy-6-methyl-2,4-dioxotetrahydropteridine, Chem.Ber. 90: 2588 (1957).

    Article  CAS  Google Scholar 

  25. M. Lederer, Les Pigments des Invertébrés (à l’Exception des Pigments Respi-ratoires), Biol.Rev. Cambridge Phil.Soc. 15: 273 (1940).

    Article  CAS  Google Scholar 

  26. M. Viscontini, E. Hadron and P. Karrer, Fluoreszierende Stoffe aus Drosophila melanogaster: die roten Augenfarbstoffe, Helv.Chim. Acta 40: 579 (1957).

    Article  CAS  Google Scholar 

  27. M. Viscontini and P. Karrer, Fluoreszierende Stoffe aus Drosophila melanogaster, Helv.Chim. Acta 40: 986 (1957).

    Google Scholar 

  28. H. Schlobach and W. Pfleiderer, Die physikalischen Eigenschaften der roten Augenpigmente aus Drosophila melanogaster, einer neuen Klasse atropisomerer Naturstoffe, Helv.Chim. Acta 55: 2525 (1972).

    Article  PubMed  CAS  Google Scholar 

  29. I. Schwinck and M. Mancini, The drosopterin pattern in various eye color mutants of the fruit fly Drosophila melanogaster, Arch.Genetik 46: 41 (1973).

    CAS  Google Scholar 

  30. K. Rokos and W. Pfleiderer, Isolierung, physikalische Eigenschaften und alkalischer Abbau der Augenpigmente Neodrosopterin und Aurodrosopteriaus Drosophila melanogaster, Chem.Ber. 108: 2728 (1975).

    Article  CAS  Google Scholar 

  31. M. Viscontini, Beitrag zur Konstitutionsaufklärung der Drosopterine, Helv.Chim. Acta 41:1299 (1958).

    Article  CAS  Google Scholar 

  32. H. Schlobach and W. Pfleiderer, Isolierung, Molekulargewichtsbestimmung und alkalischer Abbau von Drosopterin und Isodrosopterin-Augenpigmente der Fruchtfliege Drosophila melanogaster, Helv.Chim.Acta 55:2518(1972).

    Article  PubMed  CAS  Google Scholar 

  33. N. Theobald and W. Pfleiderer, Ein neuer Strukturvorschlag für die roten Augenpigmente Drosopterin und Isodrosopterin aus Drosophila melanogaster, Chem.Ber. 111: 3385 (1978).

    Article  CAS  Google Scholar 

  34. H.Schlobach and W. Pfleiderer, Synthese und Reaktionen von Droso-und Isodrosopterin, Helv.Chim. Acta 55: 2533 (1972).

    Article  PubMed  CAS  Google Scholar 

  35. G.J. Wiederrecht, D.R. Paton and G.M. Brown, The Isolation and Identification of an Intermediate involved in the Biosynthesis of Drosopterin in Drosophila melanogaster, J.Biol.Chem. 256: 10399 (1981).

    PubMed  CAS  Google Scholar 

  36. K.B. Jacobson, D. Dorsett, W. Pfleiderer, J.A. McCloskey, S.S. Sethi, M.V. Buchanan and I.R. Rubin A Naturally Occurring Pyrimidodiazepine in Drosophila: Chemical and Spectral Properties and Relationship to Drosopterin, Biochemistry 21: 5700 (1982).

    Article  PubMed  CAS  Google Scholar 

  37. DR. Paton and G.M. Brown, The nonenzymatic synthesis of ‘drosopterin’ from dihydropterin and 2-amino-4-oxo-6-acetyl-3H,9H-7,8-dihydropyrimido-4,5-b][l,4]diazepine, in:“Chemistry and Biology of Pteridines 1986”, B.A. Cooper and V.M. Whitehead, ed., W. de Gruyter, Berlin, New York (1986), p. 295.

    Google Scholar 

  38. W. Pfleiderer, S.J. Kim and J. Yim, The nonenzymatic Synthesis of Drosopterins, in:“Pteridines and Related Biogenic Amines and Folates”, ed., N.Blau, H.Ch. Curtius, R. Levine and J. Yim, Hanrim Publ. Co. Seoul, Korea, 1992), p. 54.

    Google Scholar 

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Authors and Affiliations

  1. Fakultät für Chemie, Universität Konstanz, D-7750, Konstanz, Germany

    Wolfgang Pfleiderer

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  1. Wolfgang Pfleiderer
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Editors and Affiliations

  1. Dept of Pharmacology College of Medicine, Universily of South Alabama, Mobile, AL, 36688, USA

    June E. Ayling

  2. Dept. of Biochemistry College of Medicine, University of South Alabama, Mobile, AL, 36688, USA

    M. Gopal Nair

  3. College of Medicine, Universily of South Alabama, Mobile, AL, 36688, USA

    Charles M. Baugh

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© 1993 Springer Science+Business Media New York

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Pfleiderer, W. (1993). Natural Pteridines -A Chemical Hobby. In: Ayling, J.E., Nair, M.G., Baugh, C.M. (eds) Chemistry and Biology of Pteridines and Folates. Advances in Experimental Medicine and Biology, vol 338. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-2960-6_1

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  • DOI: https://doi.org/10.1007/978-1-4615-2960-6_1

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-6287-6

  • Online ISBN: 978-1-4615-2960-6

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