Biosynthesis of drosopterins, the red eye pigments of Drosophila melanogaster

IUBMB Life

Volumn 65, Issue 4, 2013, Pages 334-340

  Kim, Heuijong ^a   Kim, Kiyoung ^a   Yim, Jeongbin ^a  

^a Seoul National University   (South Korea)

Author keywords

dihydropterin deaminase; Drosophila; drosopterins; GTPCH I; PDA synthase; PTP synthase

Indexed keywords

AURODROSOPTERIN; DEAMINASE; DIHYDROPTERIN DEAMINASE; DROSOPHILA PROTEIN; DROSOPTERIN; GUANOSINE TRIPHOSPHATE CYCLOHYDROLASE I; ISOAURODROSOPTERIN; ISODROSOPTERIN; PDA SYNTHASE; PTERIN DERIVATIVE; PTP SYNTHASE; SEPIAPTERIN; SYNTHETASE; UNCLASSIFIED DRUG;

CHROMOSOME; DROSOPHILA MELANOGASTER; IN VIVO STUDY; NONHUMAN; PIGMENT EPITHELIUM; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; REVIEW;

ANIMALS; DROSOPHILA MELANOGASTER; EYE; GTP CYCLOHYDROLASE; MUTATION; PIGMENTS, BIOLOGICAL; PTERIDINES;

EID: 84875340757     PISSN: 15216543     EISSN: 15216551     Source Type: Journal    
DOI: 10.1002/iub.1145     Document Type: Review

References (45)

1. Ziegler, I., and, Harmsen, R., (1970) The biology of pteridines in insects. Adv. Insect Physiol. 6, 139-203.
2. Wiederrecht, G., Paton, D. R., and, Brown, G. M., (1984) Enzymatic conversion of dihydroneopterin triphosphate to the pyrimidodiazepine intermediate involved in the biosynthesis of the drosopterins in Drosophila melanogaster. J. Biol. Chem. 259, 2195-2200.
3. Lederer, E., (1940) Les pigments des invertébrés. Biol. Rev. Camb. Philos. Soc. 15, 273-306.
4. Yim, J., Kim, S., Walcher, G., and, Pfleiderer, W., (1993) Pteridines. Part C. Structure and nonenzymatic synthesis of aurodrosopterin. Helv. Chim. Acta 76, 1970-1979.
5. Theobald, N., and, Pfleiderer, W., (1978) Pteridine, LXV: ein neuer strukturvorschlag fur die roten augenpigmente drosopterin und isodrosopterin aus Drosophila melanogaster. Chem. Ber. 111, 3385-3402.
6. Schlobach, H., and, Pfleiderer, W., (1972) Isolierung, molekulargewichtsbestimmung und alkalischer abbau von drosopterin und isodrosopterin-augenpigmente der fruchtfliege Drosophila melanogaster. Helv. Chim. Acta 55, 2518-2525.
7. Kim, J., Park, S. I., Ahn, C., Kim, H., and, Yim, J., (2009) Guanine deaminase functions as dihydropterin deaminase in the biosynthesis of aurodrosopterin, a minor red eye pigment of Drosophila. J. Biol. Chem. 284, 23426-23435.
8. Mackay, W. J., and, O'Donnell, J. M., (1983) A genetic analysis of the pteridine biosynthetic enzyme, guanosine triphosphate cyclohydrolase, in Drosophila melanogaster. Genetics 105, 35-53.
9. Krivi, G. G., and, Brown, G. M., (1979) Purification and properties of the enzymes from Drosophila melanogaster that catalyze the synthesis of sepiapterin from dihydroneopterin triphosphate. Biochem. Genet. 17, 371-390.
10. Park, Y. S., Kim, J. H., Jacobson, K. B., and, Yim, J. J., (1990) Purification and characterization of 6-pyruvoyl-tetrahydropterin synthase from Drosophila melanogaster. Biochim. Biophys. Acta 1038, 186-194.
11. Kim, J., Suh, H., Kim, S., Kim, K., Ahn, C., et al. (2006) Identification and characteristics of the structural gene for the Drosophila eye colour mutant sepia, encoding PDA synthase, a member of the Omega class glutathione S-transferases. Biochem. J. 398, 451-460.
12. Paton, D., and, Brown, G., (1986) The nonenzymatic synthesis of 'drosopterins' from dihydropterin and 2-amino-4-oxo-6-acetyl-3H, 9H-7,8-dihydropyrimido[4, 5b][1, 4]. Chemistry and biology of pteridinesdiazepine. In Chemistry and Biology of Pteridines. (, Cooper, B. A., and, Whitehead, V. M., eds.). pp. 295-298, Walter de Gruyter, Berlin, Germany.
13. Yim, J. J., Jacobson, K. B., and, Crummett, D. C., (1981) Detection And Some Properties Of An Enzyme From Drosophila melanogaster that releases the side chain from dihydroneopterin triphosphate. Insect Biochem. 11, 363-370.
14. Takikawa, S. I., Tsusué, M., and, Gyure, W. L., (1983) Characterization of a dihydropterin deaminase from Drosophila melanogaster. Insect Biochem. 13, 361-368.
15. Thony, B., Auerbach, G., and, Blau, N., (2000) Tetrahydrobiopterin biosynthesis, regeneration and functions. Biochem. J. 347 Pt 1, 1-16.
16. Fan, C. L., and, Brown, G. M., (1976) Partial purification and properties of guanosine triphosphate cyclohydrolase from Drosophila melanogaster. Biochem. Genet. 14, 259-270.
17. Weisberg, E. P., and, O'Donnell, J. M., (1986) Purification and characterization of GTP cyclohydrolase I from Drosophila melanogaster. J. Biol. Chem. 261, 1453-1458.
18. Nar, H., Huber, R., Meining, W., Schmid, C., Weinkauf, S., et al. (1995) Atomic structure of GTP cyclohydrolase I. Structure 3, 459-466.
19. Reynolds, E. R., and, O'Donnell, J. M., (1988) Characterization of new Punch mutations: identification of two additional mutant classes. Genetics 119, 609-617.
20. Funderburk, C. D., Bowling, K. M., Xu, D., Huang, Z., and, O'Donnell, J. M., (2006) A typical N-terminal extensions confer novel regulatory properties on GTP cyclohydrolase isoforms in Drosophila melanogaster. J. Biol. Chem. 281, 33302-33312.
21. McLean, J. R., Krishnakumar, S., and, O'Donnell, J., (1993) Multiple mRNAs from the Punch locus of Drosophila melanogaster encode isoforms of GTP cyclohydrolase I with distinct N-terminal domains. J. Biol. Chem. 268, 27191-27197.
22. Byun, J., Yoon, J., and, Baek, K., (2009) Analysis of two promoters that control the expression of the GTP cyclohydrolase I Gene in Drosophila melanogaster. Mol. Cells 27, 583-589.
23. Harada, T., Kagamiyama, H., and, Hatakeyama, K., (1993) Feedback regulation mechanisms for the control of GTP cyclohydrolase I activity. Science 260, 1507-1510.
24. Milstien, S., Jaffe, H., Kowlessur, D., and, Bonner, T. I., (1996) Purification and cloning of the GTP cyclohydrolase I feedback regulatory protein, GFRP. J. Biol. Chem. 271, 19743-19751.
25. Fan, C. L., Hall, L. M., Skrinska, A. J., and, Brown, G. M., (1976) Correlation of guanosine triphosphate cyclohydrolase activity and the synthesis of pterins in Drosophila melanogaster. Biochem. Genet. 14, 271-280.
26. Evans, B., and, Howells, A., (1978) Control of drosopterin synthesis in Drosophila melanogaster: mutants showing an altered pattern of GTP cyclohydrolase activity during development. Biochem. Genet. 16, 13-26.
27. Yim, J. J., Grell, E., and, Jacobson, K. B., (1977) Mechanism of suppression in Drosophila: control of sepiapterin synthase at the purple locus. Science 198, 1168-1170.
28. Switchenko, A. C., Primus, J. P., and, Brown, G. M., (1984) Intermediates in the enzymic synthesis of tetrahydrobiopterin in Drosophila melanogaster. Biochem. Biophys. Res. Commun. 120, 754-760.
29. Switchenko, A., and, Brown, G. M., (1985) The enzymatic conversion of dihydroneopterin triphosphate to tripolyphosphate and 6-pyruvoyl- tetrahydropterin, an intermediate in the biosynthesis of other pterins in Drosophila melanogaster. J. Biol. Chem. 260, 2945-2951.
30. Burgisser, D. M., Thony, B., Redweik, U., Hess, D., Heizmann, C. W., et al. (1995) 6-Pyruvoyl tetrahydropterin synthase, an enzyme with a novel type of active site involving both zinc binding and an intersubunit catalytic triad motif; site-directed mutagenesis of the proposed active center, characterization of the metal binding site and modelling of substrate binding. J. Mol. Biol. 253, 358-369.
31. Kim, N., Kim, J., Park, D., Rosen, C., Dorsett, D., et al. (1996) Structure and expression of wild-type and suppressible alleles of the Drosophila purple gene. Genetics 142, 1157-1168.
32. Jacobson, K. B., Dorsett, D., Pfleiderer, W., McCloskey, J. A., Sethi, S. K., et al. (1982) A naturally occurring pyrimidodiazepine in Drosophila: chemical and spectral properties and relationship to drosopterin. Biochemistry 21, 5700-5706.
33. Wilson, T. G., and, Jacobson, K. B., (1977) Isolation and characterization of pteridines from heads of Drosophila melanogaster by a modified thin-layer chromatography procedure. Biochem. Genet. 15, 307-319.
34. Wiederrecht, G., and, Brown, G. M., (1984) Purification and properties of the enzymes from Drosophila melanogaster that catalyze the conversion of dihydroneopterin triphosphate to the pyrimidodiazepine precursor of the drosopterins. J. Biol. Chem. 259, 14121-14127.
35. Giordano, E., Peluso, I., Rendina, R., Digilio, A., and, Furia, M., (2003) The clot gene of Drosophila melanogaster encodes a conserved member of the thioredoxin-like protein superfamily. Mol. Genet. Genomics 268, 692-697.
36. Board, P. G., Coggan, M., Chelvanayagam, G., Easteal, S., Jermiin, L. S., et al. (2000) Identification, characterization, and crystal structure of the omega class glutathione transferases. J. Biol. Chem. 275, 24798-24806.
37. Hama, T., (1963) The relation between the chromatophores and pterin compounds. Ann. N. Y. Acad. Sci. 100, 977-986.
38. Kaufman, S., (1958) A new cofactor required for the enzymatic conversion of phenylalanine to tyrosine. J. Biol. Chem. 230, 931-939.
39. Nagatsu, T., Levitt, M., and, Udenfriend, S., (1964) Tyrosine hydroxylase. The initial step in norepinephrine biosynthesis. J. Biol. Chem. 239, 2910-2917.
40. Tietz, A., Lindberg, M., and, Kennedy, E. P., (1964) A new pteridine-requiring enzyme system for the oxidation of glyceryl ethers. J. Biol. Chem. 239, 4081-4090.
41. Lovenberg, W., Jequier, E., and, Sjoerdsma, A., (1967) Tryptophan hydroxylation: measurement in pineal gland, brainstem, and carcinoid tumor. Science 155, 217-219.
42. Brown, G. M., and, Williamson, J. M., (2006) Biosynthesis of riboflavin, folic acid, thiamine, and pantothenic acid. In Advances in Enzymology and Related Areas of Molecular Biology, Volume 53. (, Meister, A., ed.). pp. 345-381, John Wiley and Sons, Inc., Hoboken, NJ.
43. Huennekens, F., and, Osborn, M., (2006) Folic acid coenzymes and one-carbon metabolism. In Advances in Enzymology and Related Areas of Molecular Biology, Volume 21. (, Nord, F. F., ed.). pp. 369-446, John Wiley and Sons, Inc., Hoboken, NJ.
44. Ghisla, S., and, Edmondson, D. E., (2009) Flavin coenzymes. In Encyclopedia of Life Sciences (eLS). pp. 1-9, John Wiley and Sons, Ltd., Chichester.
45. Dorsett, D., Yim, J. J., and, Jacobson, K. B., (1979) Biosynthesis of "drosopterins" by an enzyme system from Drosophila melanogaster. Biochemistry 18, 2596-2600.