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References

  • 1
    Kaufman, S. ( 1963) The structure of the phenylalanine-hydroxylation cofactor. Proc. Natl. Acad. Sci. U. S. A. 50, 10851093.
  • 2
    Kaufman, S. ( 1987) Tetrahydrobiopterin and hydroxylation systems in health and disease. In Unconjugated Pterins in Neurobiology. ( Lovenberg, W. and Levine, R. A., eds.). pp. 128, Taylor & Francis, London.
  • 3
    Fitzpatrick, P. F. ( 1999) Tetrahydropterin-dependent amino acid hydroxylases. Annu. Rev. Biochem. 68, 355381.
  • 4
    Taguchi, H. and Armarego, W. L. F. ( 1998) Glyceryl-ether monooxygenase [EC 1.14.16.5]. A microsomal enzyme of ether lipid metabolism. Med. Res. Rev. 18, 4389.
  • 5
    Kwon, N. S., Nathan, C. F., and Stuehr, D. J. ( 1989) Reduced biopterin as a cofactor in the generation of nitrogen oxides by murine macrophages. J. Biol. Chem. 264, 2049620501.
  • 6
    Tayeh, M. A. and Marletta, M. A. ( 1989) Macrophage oxidation of L-arginine to nitric oxide, nitrite, and nitrate. Tetrahydropterin is required as a cofactor. J. Biol. Chem. 264, 1965419658.
  • 7
    Crane, B. R., Arvai, A. S., Ghosh, D. K., Wu, C., Getzoff, E. D. et al. ( 1998) Structure of nitric oxide synthase dimer with pterin and substrate. Science 5359, 21212126.
  • 8
    Patterson, E. L., Broquist, H. P., Albrecht, A. M., von Saltza, M. H., and Stokstad, E. L. R. ( 1955) A new pteridine in urine required for the growth of the protozoon Crithidia fasciculata. J. Am. Chem. Soc. 77, 31673168.
  • 9
    Goto, M., Forrest, H. S., Dickerman, L. H., and Urushibara, T. ( 1965) Isolation of a new naturally occurring pteridine from bacteria, and its relation to folic acid biosynthesis. Arch. Biochem. Biophys. 111, 814.
  • 10
    Butenandt, A. and Rembold, H. ( 1958) Isolierung von 2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridin. Hoppe Seyler's Z. Physiol Chem. 311, 7983.
  • 11
    Viscontini, M., Schmid, H., and Hadorn, E. ( 1955) Isolierung fluoreszierender Stoffe aus Astacus fluviatilis. Experientia 11, 390394.
  • 12
    Mori, Y., Matsumoto, J., and Hama, T. ( 1960) On the properties of cyprino-pourpre A2, a pterin isolated from the skin of Cyprinidae, and its relation to ichthyopterin or 7-hydroxybiopterin. Z. vergl Physiol 43, 531543.
  • 13
    Hama T. and Okiba, M. ( 1960) Pterin synthesis in the amphibian neural crest cell. Nature 187, 326327.
  • 14
    Forrest, H. S., van Baalen, C., and Myers, J. ( 1958) Isolation and identification of a new pteridine from a blue-green alga. Arch. Biochem. Biophys. 78, 9599.
  • 15
    Matsunaga, T., Burgess, J. G., Yamada, N., Komatsu, K., Yoshida, S., et al. ( 1993) An ultraviolet (UV-A) absorbing biopterin glucoside from the marine planktonic cyanobacterium Oscillatoria sp. Appl. Microbiol. Biotechnol. 39, 250253.
  • 16
    Noguchi, Y., Ishii, A., Matsushima, A., Haishi, D., Yasumuro, K., et al. ( 1999) Isolation of biopterin-α-glucoside from Spirulina (Arthrospira) platensis and its physiologic function. Mar. Biotechnol. 1, 207210.
  • 17
    Choi, Y. K., Hwang, Y. K., Kang, Y. H., and Park, Y. S. ( 2001) Chemical structure of 1-O-(L-erythro-biopterin-2′-yl)- α-glucose isolated from a cyanobacterium Synechococcus sp. PCC 7942. Pteridines 12, 121125.
  • 18
    Hanaya, T., Torigoe, K., Soranaka, K., Fujita, H., Yamamoto, H., et al. ( 2008) An efficient synthesis of 2′-O-(β-D-ribofuranosyl)biopterin. Pteridines 19, 7278.
  • 19
    Cha, K. W., Pfleiderer, W., and Yim, J. J. ( 1995) Isolation and characterization of limipterin (1-O-(L-erythro-biopterin-2′-yl)-β-N-acetylglucosamine) and its 5,6,7,8-tetrahydro derivative from green sulfur bacterium Chlorobium limicola f. thiosulfatophilum NCIB 8327. Helv. Chim. Acta 78, 600614.
  • 20
    Ikawa, M., Sasner, J. J., Haney, J. F., and Foxall, T. L. ( 1995) Pterins of the cyanobacterium Aphanizomenon flos-aquae. Phytochemistry 38, 12291232.
  • 21
    Cho, S.-H., Na, J.-U., Youn, H., Hwang, C.-S., Lee, C.-H., et al. ( 1998) Tepidopterin, 1-O-(L-threo-biopterin-2′-yl)-β-N-acetylglucosamine from Chlorobium tepidum. Biochim. Biophys. Acta 1379, 5360.
  • 22
    Suzuki, R. and Goto, M. ( 1968) Neopterin-3′-β-D-glucuronide: isolation from Azotobacter agilis. J. Biochem. 63, 798801.
  • 23
    Kobayashi, K. and Forrest, H. S. ( 1970) Isolation and identification of a new pteridine neopterinyl-3′-β-D-glucuronic acid from Bacillus subtilis. Comp. Biochem. Physiol. 33, 201207.
  • 24
    Lin, X. and White, R. H. ( 1988) Structure of solfapterin (erythro-neopterin-3′-D-2-deoxy-2-aminoglucopyranoside) isolated from the thermophilic archaebacterium Sulfolobus solfataricus. J. Bacteriol. 170, 13961398.
  • 25
    Hatfield, D. L., van Baalen, C., and Forrest, H. S. ( 1961) Pteridines in blue green algae. Plant Physiol. 36, 240243.
  • 26
    Lee, H. W., Oh, C. H., Geyer, A., Pfleiderer, W., and Park, Y. S. ( 1999) Characterization of a novel unconjugated pteridine glycoside, cyanopterin, in Synechocystis sp. PCC 6803. Biochim. Biophys. Acta 1410, 6170.
  • 27
    Goto, M., Kobayashi, K., Sato, H., and Korte, F. ( 1965) Ein neues Pteridin aus Mycobacterium smegmatis. Liebig's Ann. Chem. 689, 221228.
  • 28
    Kaneko, Y. and Sanada, M. ( 1969) Studies on the fluorescent substances produced by Aspergillus fungi (VIII). Purification and isolation of Asperopterin B and chemical properties of asperopterin B and A. J. Ferment. Technol. 47, 819.
  • 29
    Wachi, Y., Yoshida, S., Komatsu, K., and Matsunaga, T. ( 1993) Biopterin glycoside, its manufacture with algae, and its use in cosmetic skin preparations. Jpn. Patent, 05,286,989 ( Chem. Abstr., 1994, 120, 161782t).
  • 30
    Saito, T., Ishikawa, H., Hada, Y., Fukui, K., Kodera, Y., et al. ( 2003) Photostabilization of phycocyanin and anthocyanin in the presence of biopterin-α-glucoside from Spirulina platensis. Dyes Pigments 56, 203207.
  • 31
    Pfleiderer, W. ( 1963) The solubility of heterocyclic compounds. In Physical methods in heterocyclic chemistry. ( Katritzky, A. R. ed.) Vol. 1, pp. 177188, Academic Press, New York.
  • 32
    Hanaya, T., Torigoe, K., Soranaka, K., Yamamoto, H., Yao, Q., et al. ( 1995) Selective N(3)- and O4-alkylation of L-biopterin: a convenient synthesis of 3- and O4-methyl-L-biopterin and the versatile N2-(N,N-dimethylaminomethylene)-N(3)-p-nitrophenethyl-protected L-biopterin. Pteridines 6, 17.
  • 33
    Hanaya, T., Soranaka, K., Harada, K., Yamaguchi, H., Suzuki, R., et al. ( 2006) An efficient synthesis of 2′-O-(β-D-glucopyranosyl)- and 2′-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-biopterins. Heterocycles 67, 299310.
  • 34
    Ness, R. K., FletcherJr.,H. G., and Hudson, C. S. ( 1950) The Reaction of 2,3,4,6-tetrabenzoyl-α-D-glucopyranosyl bromide and 2,3,4,6-tetrabenzoyl-α-D-mannopyranosyl bromide with methanol. Certain benzoylated derivatives of D-glucose and D-mannose. J. Am. Chem. Soc. 72, 22002205.
  • 35
    Hanaya, T., Toyota, H., and Yamamoto, H. ( 2006) Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L-biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides. Synlett 20752078.
  • 36
    Hanaya, T., Baba, H., Toyota, H., and Yamamoto, H. ( 2008) Efficient total syntheses of natural pterin glycosides: limipterin and tepidopterin. Tetrahedron 64, 20902100.
  • 37
    Kiss, J., D'Souza, R., and Taschner, P. ( 1975) Präparative Herstellung von 5-Desoxy-L-arabinose, Xylit und D-Ribose aus Diacetonglucose. Helv. Chim. Acta 58, 311317.
  • 38
    Farkas, J., Ledvina, M., Brokes, J., Jezek, J., Zajicek, J., et al. ( 1987) The synthesis of O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1[RIGHTWARDS ARROW]4)-N-acetylnormuramoyl-l-α-aminobutanoyl-D-isoglutamin. Carbohydr. Res., 163 6372.
  • 39
    Hanaya, T., Baba, H., Kanemoto, M., and Yamamoto, H. ( 2008) An efficient synthetic route for a versatile ciliapterin derivative and the first ciliapterin D-mannoside synthesis. Heterocycles 76, 635644.
  • 40
    Wulff, G. and Röhle, G. ( 1974) Results and problems of O-glycoside synthesis. Angew. Chem., Int. Ed. Engl. 13, 157170.
  • 41
    Hanaya, T., Baba, H., Toyota, H., and Yamamoto, H. ( 2009) Synthetic studies on pterin glycosides: the first synthesis of 2′-O-(α-D-glucopyranosyl)biopterin. Tetrahedron 65, 79897997.
  • 42
    Hanaya, T., Hattori, T., Takayama, D., and Yamamoto, H. ( 2010) First synthesis of a natural neopterin glycosides: 3′-O-(β-D-glucopyranosyluronic acid)neopterin. Pteridines 21, 7983.
  • 43
    Zorbach, W. W. and Valiaveedan, G. D. ( 1964) Methyl (cortison-21-yl 2,3,4-tri-O-acetyl-β-D-glucosid)uronate. J. Org. Chem. 29, 24622463.
  • 44
    Hanaya, T., Ejiri, K., and Yamamoto, H. ( 2012) First synthesis of a natural isoxanthopterin glycoside, asperopterin-A. Heterocycles, 84, 801813.
  • 45
    Pfleiderer, W. and Rukwied, M. ( 1961) Zur Struktur des Isoxanthopterins. Chem. Ber. 94, 112.
  • 46
    Sugimoto, T., Murata, S., Matsuura, S., and Pfleiderer, W. ( 1986) Synthesis of asperopterin-B and some analogues. Tetrahedron Lett. 27, 41794180.
  • 47
    Matsuura, S., Yamamoto, M., and Kaneko, Y. ( 1972) The structure of the pteridine glycoside from Aspergillus oryzae. Bull. Chem. Soc. Jpn. 45, 492495.
  • 48
    Hanaya, T., Baba, H., Ejiri, K., and Yamamoto, H. ( 2010) Synthesis of 6-hydroxymethylpterin α- and β-D-glucosides. Heterocycles 80, 10131025.
  • 49
    Kang, D., Kim, S., and Yim, J. ( 1998) Biosynthetic enzymes of tetrahydrolimipterin from green sulfur bacterium Chlorobium limicola. Pteridines 9, 6984.
  • 50
    Chung, H. L., Kim, Y.-A., Kim, Y. J., Choi, Y. K., Hwang, Y. K., et al. ( 2000) Purification and characterization of UDP-glucose: tetrahydrobiopterin glucosyltransferase from Synechococcus sp. PCC 7942. Biochim. Biophys. Acta 1542, 183188.