Abstract
Nucleosides, in which a carbohydrate unit is linked to a heterocyclic base, are fundamental components of nucleic acids and nucleotide coenzymes, where they occur in phosphorylated form. In most nucleosides the sugar, either D-ribose or 2-deoxy-D-erythro pentose (“2-deoxyribose”), is linked to a nitrogen atom of a pyrimidine or purine, as in the ribonucleosides uridine (1) and adenosine (2).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Cohn, W. E., and E. Volkin: Nucleoside-S’-Phosphates from Ribonucleic Acid. Nature 167, 483 (1951).
Davis, F. F., and F. W. Allen: Ribonucleic Acids from Yeast which Contain a Fifth Nucleotide. J. Biol. Chem. 227, 907 (1957).
Cohn, W. E.: Pseudouridine, a Carbon-Carbon Linked Ribonucleoside in Ribonucleic Acids: Isolation, Structure, and Chemical Characteristics. J. Biol. Chem. 235, 1488 (1960).
Michelson, A. M., and W. E. Cohn: Cyclo-pseudouridine and the Configuration of Pseudouridine. Biochemistry 1, 490 (1962).
Yu, C.-T., and F. W. Allen: Studies on an Isomer of Uridine Isolated from Ribonucleic Acids. Biochim. Biophys. Acta 32, 393 (1959).
Chambers, R. W.: The Chemistry of Pseudouridine. Progr. Nucleic Acid Res. Mol. Biol. 5, 349 (1966).
Adler, M., and A. B. Gutman: Uridine Isomer (5-Ribosyluracil) in Human Urine. Science 130, 862 (1959).
Uematsu, T., and R. J. Suhadolnik: Pseudouridine, Isolation and Biosynthesis of the Nucleoside isolated from the Culture Filtrates of Streptoverticillicum Ladakanus. Biochemistry 11, 4669 (1972).
Argoudelis, A. D., and S. A. Mizsak: 1-Methylpseudouridine, a Metabolite of Streptomyces Platensis. J. Antibiotics 29, 818 (1976).
fox, J. J., K. A. Watanabe, and A. Bloch: Nucleoside Antibiotics. Progr. Nucleic Acid Res. Mol. Biol. 5, 251 (1966).
Suhadolnik, R. J.: Nucleoside Antibiotics. New York: J. Wiley. 1970.
Suhadolnik, R. J.: Nucleosides as Biological Probes. New York: J. Wiley. 1979.
Suhadolnik, R. J.: Naturally Occurring Nucleoside and Nucleotide Antibiotics. Progr. Nucleic Acid Res. Mol. Biol. 22, 193 (1979).
Buchanan, J. G., and R. H. Wightman: Chemistry of Nucleoside Antibiotics. IN: Topics in Antibiotic Chemistry, 6 (P. G. Sammes, ed.), p. 229. Chichester: E. Horwood. 1982.
Goodchild, J.: The Biochemistry of Nucleoside Antibiotics. In: Topics in Antibiotic Chemistry, 6 (P. G. Sammes, ed.), p. 99. Chichester: E. Horwood. 1982.
Tronchet, J. M. J.: Synthèse de Nouveaux Types de C-Nucléosides. Biol. Med. 4, 83 (1975).
Hanessian, S., and A. G. Pernet: Synthesis of Naturally Occurring C-Nucleosides, their Analogs, and Functionalised C-Glycosyl Precursors. Adv. Carbohydrate Chem. Biochem. 33, 111 (1976).
Daves, G. D., JR., and C. C. Cheng: The Chemistry and Biochemistry of C-Nucleosides. Progr. Medicin. Chem. 13, 303 (1976).
Michelson, A. M.: The Chemistry of Nucleosides and Nucleotides. New York: Academic Press. 1963.
Lemieux, R. U.: Rearrangements and Isomerizations in Carbohydrate Chemistry. In: Molecular Rearrangements, Part 2 (P. de Mayo, ed.), pp. 710–719. New York: J. Wiley. 1964.
Brown, D. M., M. G. Burdon, and R. P. Slatcher: A Synthesis of Pseudouridine and 5-P-D-Ribofuranosyluridine. J. Chem. Soc. (C) 1968, 1051.
Lerch, U., M. G. Burdon, and J. G. Moffatt: C-Glycosyl Nucleosides. I. Studies on the Synthesis of Pseudouridine and Related Compounds. J. Organ. Chem. (USA) 36, 1507 (1971).
Brown, D. M., and R. C. Ogden: A Synthesis of Pseudouridine. J. Chem. Soc. Perkin I 1981, 723.
Baron, F., and D. M. Brown: Nucleotides. Part XXXIII. The Structure of Cytidylic Acids a and b. J. Chem. Soc. ( London ) 1955, 2855.
Darnall, K. R., L. B. Townsend, and R. K. Robins: The Structure of Showdomycin, a Novel Carbon-Linked Nucleoside Antibiotic Related to Uridine. Proc. Nat. Acad. Sci. (USA) 57, 548 (1967).
Sasaki, K., Y. Kusakabe, and S. Esumi: The Structure of Minimycin, a Novel Carbon- linked Nucleoside Antibiotic Related to p-Pseudouridine. J. Antibiotics 25, 151 (1972).
Townsend, L. B.: Nuclear Magnetic Resonance Spectroscopy in the Study of Nucleic Acid Components and Certain Related Derivatives. In: Synthetic Procedures in Nucleic Acid Chemistry, Vol. 2 (W. W. Zorbach and R. S. Tipson, eds.), p. 267. New York: J. Wiley. 1973.
Rice, J. M., and G. O. Dudek: Mass Spectra of Uridine and Pseudouridine: Fragmentation Patterns Characteristic of a Carbon-Carbon Nucleoside Bond. Biochem. Biophys. Res. Comm. 35, 383 (1969).
Deslauriers, R., and I. C. P. Smith: A Comparison of the Conformations of Uridine, (3- Pseudouridine, and Dihydrouridine in Dimethyl Sulfoxide and Water. A 1H Nuclear Magnetic Resonance Study. Canad. J. Chem. 51, 833 (1973).
Robins, R. K., L. B. Townsend, F. Cassidy, J. F. gerster, A. F. Lewis, and R. L. Miller: Structure of the Nucleoside Antibiotics Formycin, Formycin B and Laurusin. J. Hetero. Chem. 3, 110 (1966).
Nakagawa, Y., H. Kano, Y. Tsukuda, and H. Koyama: Structure of a New Class of C- Nucleoside Antibiotic, Showdomycin. Tetrahedron Letters 1967, 4105.
Koyama, G., K. Maeda, H. Umezawa, and Y. Iitaka: The Structural Studies of Formycin and Formycin B. Tetrahedron Letters 1966, 597.
Gutowski, G. E., M. O. Chaney, N. D. Jones, R. L. Hamill, F. A. Davies, and R. D. Miller: Pyrazomycin B: Isolation and Characterization of an A-C-Nucleoside Antibiotic Related to Pyrazomycin. Biochem. Biophys. Res. Comm. 51, 312 (1973).
Haneishi, T., T. Okazaki, T. Hata, C. Tamura, M. Nomura, A. Naito, I. Seki, and M. Arai: Oxazinomycin, a New Carbon-linked Nucleoside Antibiotic. J. Antibiotics 24, 797 (1971).
Sakata, K., A. Sakurai, and S. Tamura: Studies on Ezomycins, Antifungal Antibiotics, Part X. Structures of Ezomycins B1, B2, C1, C2, and D2. Agr. Biol. Chem. 41, 2033 (1977).
Wenkert, E.S E. W. Hagaman, and G. E. Gutowski: Carbon-13 Nuclear Magnetic Resonance Spectral Analysis of C-Nucleosides. The Structure of Pyrazomycin B. Biochem. Biophys. Res. Comm. 51, 318 (1973).
Chenon, M.-T., R. J. Pugmire, D. M. Grant, R. P. Panzicka, and L. B. Townsend: Carbon-13 NMR Spectra of C-Nucleosides. Showdomycin and p-Pseudouridine. J. Hetero. Chem. 10, 427 (1973).
Isono, K., and J. Uzawa: 13C-Nmr Evidence for the Biosynthetic Incorporation of Acetate into Minimycin and Compounds Related to Krebs Cycle. FEBS Letters 80, 53 (1977).
Hruska, F. E., A. A. Grey, and I. C. P. Smith: A Nuclear Magnetic Resonance Study of the Molecular Conformation of (3-Pseudouridine in Aqueous Solution. J. Amer. Chem. Soc. 92, 4088 (1970).
Jones, A. J., D. M. Grant, M, W. Winkley, and R. K. Robins: Pyrimidine and Purine Nucleosides. J. Amer. Chem. Soc. 92, 4079 (1970).
Dejongh, D. C.: Mass Spectrometry of Nucleic Acid Components. In: Synthetic Procedures in Nucleic Acid Chemistry, Vol. 2 (W. W. Zorbach and R. S. Tipson), p. 145. New York: J. Wiley. 1973.
Townsend, L. B., and R. K. ROBINS: The Mass Spectra of Formycin, Formycin B and Showdomycin, Carbon Linked Nucleoside Antibiotics. J. Hetero. Chem. 6, 459 (1969). Crain, P. F., J. A. Mccloskey, A. F. Lewis, K. H. Schram, and L. B. Townsend: Mass Spectra of C-Nucleosides II. An Unusual Fragmentation Reaction of the Heterocyclic Moiety of Pyrazomycin and Some Closely Related Compounds. J. Hetero. Chem. 10, 843 (1973).
Farkas, J., Z. Flegelova, and F. Sorm: Synthesis of Pyrazomycin. Tetrahedron Letters 1972, 2279.
Ulbricht, T. L. V.: Optical Rotatory Dispersion of Nucleosides and Nucleotides. In: Synthetic Procedures in Nucleic Acid Chemistry, Vol. 2 (W. W. Zorbach and R. S. Tipson), p. 177. New York: J. Wiley. 1973.
Davies, D. B.: Conformations of Nucleosides and Nucleotides. Progr. NMR Spectroscopy 12, 135 (1978).
Nishimura, H., M. mayama, Y. Komatsu, H. kato, N. Shimaoka, and Y. Tanaka: Showdomycin, a New Antibiotic from a Streptomyces Sp. J. Antibiotics Ser. A 17, 148 (1964).
Tsukuda, Y., Y. Nakagawa, H. Kano, T. Sato, M. Shiro, and H. koyama: The Crystal Structure of Showdomycin and their Derivatives. Chem. Commun. 1967, 975.
Kalvoda, L., J. Farkas, and F. Sorm: Synthesis of Showdomycin. Tetrahedron Letters 1970, 2297.
Kalvoda, L.: Simple Preparative Synthesis of Showdomycin. J. Carbohydrates, Nucleosides, Nucleotides 3, 47 (1976).
Bobek, M., and J. Farkas: Nucleic Acid Components and their Analogues. CXVIII. Synthesis of 8-P-D-Ribofuranosyladenine Starting from 2,5-Anhydro-D-allonic Acid. Collect. Czech. Chem. Comm. 34, 247 (1969).
Kalvoda, L.: The Synthesis of Pyrazoles. A Simple Preparative Synthesis of C-Nucleosidic Antibiotics Formycin and Formycin B. Collect. Czech. Chem. Comm. 43, 1431 (1978).
Trummlitz, G., and J. G. Moffatt: C-Glycosyl Nucleosides. III. A Facile Synthesis of the Nucleoside Antibiotic Showdomycin. J. Organ. Chem. (USA) 38, 1841 (1973).
Albrecht, H. P., D. B. Repke, and J. G. Moffatt: C-Glycosyl Nucleosides. II. A Facile Synthesis of Derivatives of 2,5-Anhydro-D-allose. J. Organ. Chem. (USA) 38, 1836 (1973).
Buchanan, J. G., A. R. Edgar, and M. J. Power: C-Nucleoside Studies. Part 1. Synthesis of [2,3,5-Tri-0-benzyl-a(and P)-D-ribofuranosyl]ethyne. J. Chem. Soc. Perkin I 1974, 1943.
Buchanan, J. G., A. R. Edgar, M. J. Power, and C. T. Shanks: C-Nucleoside Studies. Part 7. A New Synthesis of Showdomycin, 2-P-D-Ribofuranosylmaleimide. J. Chem. Soc. Perkin I 1979, 225.
Barker, R., and H. G. Fletcher, JR.: 2,3,5-Tri-O-benzyl-D-ribosyl and -L-arabinosyl bromides. J. Organ. Chem. (USA) 26, 4605 (1961).
Heck, R. F.: Dicarboalkoxylation of Olefins and Acetylenes. J. Amer. Chem. Soc. 94, 2712 (1972).
Inoue,T., and I. Kuwajima: Highly Efficient Method for the Synthesis of Showdomycin. Chem. Commun. 1980, 251.
Just, G., A. Martel, K. Grozinger, and M. Ramjeesingh: C-Nucleosides and Related Compounds. IV. The Synthesis and Chemistry of D,L-2,5-Anhydroallose Derivatives. Canad. J. Chem. 53, 131 (1975).
Just, G., T. J. Liak, M.-I. Lim, P. Potvin, and Y. S. Tsantrizos: C-Nucleosides and Related Compounds. XV. The Synthesis of D,L-e/-Showdomycin and D,L- Showdomycin. Canad. J. Chem. 58, 2024 (1980).
Ito, Y., T. Shibata, M. Arita, H. Sawai, and M. Ohno: Chirally Selective Synthesis of Sugar Moiety of Nucleosides by Chemicoenzymatic Approach: L- and D-Riboses, Showdomycin, and Cordycepin. J. Amer. Chem. Soc. 103, 6739 (1981).
Just, G., and A. Martel: C-Nucleosides and Related Compounds. Synthesis of D,L-3,4- 0-Isopropylidene-2,5-anhydroallose: A Novel Periodate Cleavage. Tetrahedron Letters 1973, 1517.
Just, G., and K. Grozinger: A Correction to “A Novel Periodate Cleavage”. Tetrahedron Letters 1974, 4165.
Aldersley, M. F., A. J. Kirby, and P. W. Lancaster: Intramolecular Displacement of Alkoxide Ions by the Ionised Carboxy-group: Hydrolysis of Alkyl Hydrogen Dialkylmaleates. J. Chem. Soc. Perkin II 1974, 1504.
Gensler, W. J., S. Chan, and D. B. Ball: Synthesis of a Triazole Homo-C-nucleoside. J. Amer. Chem. Soc. 97, 436 (1975).
Ohrui, H., G. H. Jones, J. G. Moffatt, M. L. Maddox, A. T. Christensen, and S. K. Byram: C-Glycosyl Nucleosides. V. Some Unexpected Observations on the Relative Stabilities of Compounds Containing Fused Five-Membered Rings with Epimerizable Substituents. J. Amer. Chem. Soc. 97, 4602 (1975).
Ohrui, H., and S. Emoto: A Rationalization of the Relative Thermodynamic Stabilities of Fused Five-Membered Tetrahydrofurans with Epimerizable Substituents. An Anomeric Effect in Furanoses. J. Organ. Chem. (USA) 42, 1951 (1977).
Noyori, R., T. Sato, and Y. Hayakawa: A Stereocontrolled Synthesis of C- Nucleosides. J. Amer. Chem. Soc. 100, 2561 (1978).
Sato, T., R. Ito, Y. Hayakawa, and R. NOYORI: Stereocontrolled Synthesis of Showdomycin and 6-Azapseudouridines. Tetrahedron Letters 1978, 1829.
Chu, C. K., I. Wempen, K. A. Watanabe, and J. J. Fox: Nucleosides, 100. General Synthesis of Pyrimidine C-5 Nucleosides Related to Pseudouridine. Synthesis of 5-((3-D- Ribofuranosyl)isocytosine (Pseudoisocytidine), 5-(p-D-Ribofuranosyl)-2-thiouracil (2Thiopseudouridine) and 5-(p-D-Ribofuranosyl)uracil (Pseudouridine). J. Organ. Chem. (USA) 41, 2793 (1976).
Kozikowski, A. P., and A. Ames: Total Synthesis of the C-Nucleoside //-Showdomycin by a Diels-Alder, Retrograde Dieckmann Strategy. J. Amer. Chem. Soc. 103, 3923 (1981).
Matsuura, S., O. Shiratori, and K. Katagiri: Antitumour Activity of Showdomycin. J. Antibiotics Ser. A 17, 234 (1964).
Komatsu, Y.: Mechanism of Action of Showdomycin. V. Reduced Ability of Showdomycin-resistant Mutants of Eschericia Coli K-12 to take up Showdomycin and Nucleosides. J. Antibiotics 24, 876 (1971).
Visser, D. W., and S. Roy-Burman: Showdomycin. In: Antibiotics, Vol.5, Part2. Mechanism of Action of Antieukaryotic and Antiviral Compounds (F. E. Hahn, ed.), p. 363. New York: Springer. 1979.
Ozaki, M., T. Kariya, H. Kato, and T. Kimura: Microbial Transformation of Antibiotics. Part II. omerisation of Showdomycin by Streptomyces Species. Agr. Biol. Chem. 36, 451 (1972).
Nakagawa, Y.: Personal Communication.
Hori, M., E. Ito, T. Takita, G. Koyama, T. Takeuchi, and H. Umezawa: A New Antibiotic, Formycin. J. Antibiotics Ser. A 17, 96 (1964).
Koyama, G., and H. Umezawa: Formycin B and Its Relation to Formycin. J. Antibiotics Ser. A 18, 175 (1965).
Aizawa, A., T. Hidaka, N. Otake, H. Yonehara, K. Isono, N. Igarishi, and S. Suzuki: Studies on a New Antibiotic, Laurusin. Agr. Biol. Chem. 29, 375 (1965).
Umezawa, H., T. Sawa, Y. Fukagawa, G. Koyama, M. Murase, M. Hamada, and T. Takeuchi: Transformation of Formycin to Formycin B and their Biological Activities. J. Antibiotics Ser. A 18, 178 (1965).
Otake, N., S. Aizawa, T. Hidaka, H. Seto, and H. Yonehara: Biological and Chemical Transformations of Formycin to Laurusin. Agr. Biol. Chem. 29, 377 (1965).
Fukagawa, Y., T. Sawa, T. Takeuchi, and H. Umezawa: Deamination of Purine Antibiotics by Adenosine Deaminase. J. Antibiotics Ser. A 18, 191 (1965).
Sawa, T., Y. Fukagawa, I. Homma, T. Takeuchi, and H. Umezawa: Formycin- deaminating Activity of Microorganisms. J. Antibiotics Ser. A 20, 317 (1967).
Ishizuka, M., T. Sawa, G. Koyama, T. Takeuchi, and H. Umezawa: Metabolism of Formycin and Formycin B In Vivo. J. Antibiotics 21, 1 (1968).
sawa, T., Y. Kukagawa, I. Homma, T. Wakashiro, T. Takeuchi, M. Hori, and T. Komai: Metabolic Conversion of Formycin B to Formycin A and to Oxformycin B in Nocardia Interforma. J. Antibiotics 21, 334 (1968).
Kawamura, K., S. Fukatsu, M. Murase, G. Koyama, K. Maeda, and H. Umezawa: The Studies on the Degradation Products of Formycin and Formycin B. J. Antibiotics Ser. A 19, 91 (1966).
Robins, R. K., F. W. Furcht, A. D. Grauer, and J. W. Jones: Potential Purine Antagonists. II. Synthesis of some 7- and 5,7-substituted Pyrazolo[4,3-d]pyrimidines. J. Amer. Chem. Soc. 78, 2418 (1956).
Robins, R. K., L. B. Holum, and F. W. Furcht: Potential Purine Antagonists. V. Synthesis of Some 3-Methyl-5,7-substituted Pyrazolo[4,3-d]pyrimidines. J. Organ. Chem. (USA) 21, 833 (1956).
Koyama, G., H. Umezawa, and Y. Iitaka: Crystal Structure of Formycin Hydrobromide Monohydrate. Acta Crystallogr. Sect. B 30, 1511 (1974).
Prusiner, P., T. Brennan, and M. Sundaralingam: Crystal Structure and Molecular Conformation of Formycin Monohydrates. Possible Origin of the Anomalous Circular Dichroic Spectra in Formycin Mono and Polynucleotides. Biochemistry 12, 1196 (1973).-92. Koyama, G., H. Nakamura, H. Umezawa, and Y. Iitaka: The Crystal and Molecular Structures of Oxoformycin B and Formycin B. Acta Crystallogr. Sect. B 32, 813 (1976).
Buchanan, J. G., M. R. Hamblin, G. R. Sood, and R. H. Wightman: The Biosynthesis of Pyrazofurin and Formycin. Chem. Commun. 1980, 917.
Farkas, J., and F. Sorm: Synthesis of 3-(p-D-Ribofuranosyl)-5,7-dihydroxy-l/1- pyrazolo-[4,3-d]-pyrimidine (Oxoformycin). Collect. Czech. Chem. Comm. 37, 2798 (1972). Preliminary communication: BOBEK, M., J. FARKAS, and F. SORM, Tetrahedron Letters 1970, 4611.
Acton, E. M., K. J. Ryan, D. W. Henry, and L. Goodman: Synthesis of the Nucleoside Antibiotic Formycin B. Chem. Commun. 1971, 986.
Ogawa, T., Y. Kikuchi, M. Matsui, H. Ohrui, H. Kuzuhara, and S. Emoto: Synthetic Studies on C-Nucleosides. Part I. A Synthesis of Oxoformycin. Agr. Biol. Chem. 35, 1825 (1971).
Lang, R. A., A. F. Lewis, R. K. Robins, and L. B. Townsend: Pyrazolopyrimidine Nucleosides. Part II. 7-Substituted 3-P-D-Ribofuranosylpyrazolo[4,3-d]pyrimidines Related to and Derived from the Nucleoside Antibiotics Formycin and Formycin B.J. Chem. Soc. (C) 1971, 2443.
Kalvoda, L.: The Synthesis of Pyrazoles. A Simple Preparative Synthesis of C-Nucleosidic Antibiotics Formycin and Formycin B. Collect. Czech. Chem. Comm. 43, 1431 (1978).
Buchanan, J. G., A. R. Edgar, R. J. Hutchison, A. Stobie, and R. H. Wightman: C-Nucleoside Studies. Part 10. A New Synthesis of 3-(2,3,5-Tri-0-benzyl-P-D-ribo- furanosyl)pyrazole and its Conversion into 4-Nitro-3(5)-P-D-ribofuranosylpyrazole. J. Chem. Soc. Perkin I 1980, 2567.
Buchanan, J. G., A. Stobie, and R. H. Wightman: C-Nucleoside Studies. Part XI. Cme-substitution in 1,4-Dinitropyrazoles; Application to the Synthesis of Formycin via Nitropyrazole Derivatives. Canad. J. Chem. 58, 2624 (1980).
Habraken, C. L., and E. K. Poels: Nucleophilic Substitution Reactions on N- Nitropyrazoles. J. Organ. Chem. (USA) 42, 2893 (1977).
Buchanan, J. G., A. Stobie, and R. H. Wightman: C-Nucleoside Studies. Part 14. A New Synthesis of Pyrazofurin. J. Chem. Soc. Perkin I 1981, 2374.
Ishizuka, M., T. Takeuchi, K. Nitta, G. Koyama, M. Hori, and H. Umezawa: Antitumour Activities of Formycin and Labilomycin. J. Antibiotics Ser. A 17, 124 1964 ).
Ishizuka, M., T. Sawa, S. Hori, H. Takayama, T. Takeuchi, and H. Umezawa: Biological Studies on Formycin and Formycin B. J. Antibiotics 21, 5 (1968).
Muller, W. E. G., H. J. Rohde, R. Steffen, A. Maidhof, M. Lachmann, R. K. Zahn, and H. Umezawa: Influence of Formycin B on Polyadenosine Diphosphoribose Synthesis In vitro and In vivo. Cancer Res. 35, 3673 (1975).
Hori, M. T. Wakashiro, E. Ito, T. Sawa, T. Takeuchi, and H. Umezawa: Biochemical Effects of Formycin B on Xanthomonas Oryzae. J. Antibiotics 21, 264 (1968).
Takeuchi, T., J. Iwanaga, T. Aoyagi, and H. Umezawa: Antiviral Effect of Formycin and Formycin B. J. Antibiotics Ser. A 19, 286 (1966).
Ishida, N., M. Homma, K. Kumagai, Y. Schimizu, S. Matsumoto, and A. Izawa: Studies on the Antiviral Activity of Formycin. J. Antibiotics Ser. A 20, 49 (1967).
Umezawa, H. T. Sawa, Y. Fukagawa, I. Homma, M. Ishizuka, and T. Takeuchi: Studies on Formycin and Formycin B in Cells of Ehrlich Carcinoma and E. Coli. J. Antibiotics Ser. A 20, 308 (1967).
Ward, D. C., A. Cerami, E. Reich, G. Acs, and L. Altwerger: Biochemical Studies of the Nucleoside Analogue, Formycin. J. Biol. Chem. 244, 3243 (1969).
Ikehara, M., K. Murao, F. Harada, and S. Nishimura: Synthesis of Formycin Triphosphate and its Incorporation into Ribopolynucleotide by DNA-Dependent RNA Polymerase. Biochim. Biophys. Acta 155, 82 (1968).
Maelicke, A., M. Sprinzl, F. Vonderhaar, T. A. Khwaja, and F. Cramer: Structural Studies on Phenylalanine Transfer Ribonucleic Acid from Yeast with the Spectroscopic Label Formycin. Eur. J. Biochem. 43, 617 (1974).
Ward, D. C., and E. Reich: Conformational Properties of Polyformycin: A Polyribonucleotide with Individual Residues in the Conformation. Proc. Nat. Acad. Sci (USA) 61, 1494 (1968).
Ward, D. C., W. Fuller, and E. Reich: Stereochemical Analysis of the Specificity of Pancreatic RNase with Polyformycin as Substrate: Differentiation of the Trans- phosphorylation and Hydrolysis Reactions. Proc. Nat. Acad. Sci (USA) 62, 581 (1969).
Ward, D. C., T. Horn, and E. Reich: Fluorescence Studies of Nucleotides and Polynucleotides. III. Diphosphopyridine Nucleotide Analogues which Contain Fluorescent Purines. J. Biol. Chem. 247, 4014 (1972).
von der Haar, F., and E. Gaertner: Phenylalanyl-tRNA Synthetase from Baker’s Yeast: Role of S’-Terminal Adenosine of tRNAphe in Enzyme-Substrate Interaction Studied with 3’-Modified tRNAPhe Species. Proc. Nat. Acad. Sci (USA) 72, 1378 (1975).
Kumar, S. A., J. S. Krakow, and D. C. Ward: ATP Analogues as Initiation and Elongation Nucleotides for Bacterial DNA-Dependent RNA Polymerase. Biochim. Biophys. Acta 477, 112 (1977).
Sawa, T., Y. Fukagawa, I. Homma, T. Takeuchi, and H. Umezawa: Mode of Inhibition of Coformycin on Adenosine Deaminase. J. Antibiotics Ser. A 20, 227 (1967).
Nakamura, H., G. Koyama, Y. Iitaka, M. Ohno, N. Yagisawa, S. Kondo, K. Maeda, and H. Umezawa: Structure of Coformycin, an Unusual Nucleoside of Microbial Origin. J. Amer. Chem. Soc. 96, 4327 (1974).
Ohno, M., N. Yagisawa, S. Shibahara, S. Kondo, K. Maeda, and H. Umezawa: Synthesis of Coformycin. J. Amer. Chem. Soc. 96, 4326 (1974).
Henderson, J. F., A. R. P. Paterson, I. C. Caldwell, and M. HORI: Biochemical Effects of Formycin, an Adenosine Analog. Cancer Res. 27, 715 (1967).
Gerzon, K., D. C. Delong, and J. C. Cline: C-Nucleosides: Aspects of Chemistry and Mode of Action. Pure Appl. Chem. 28, 489 (1971).
Gerzon, K., R. H. Williams, M. Hoehn, M. Gorman, and D. C. Delong: Pyrazomycin, A C-Nucleoside with Antiviral Activity. 2nd Int. Cong. Hetero. Chem., Montpellier, France, July 1969, Abstr. 30C, p. 131.
Williams, R. H., K. Gerzon, M. Hoehn, M. Gorman, and D. C. Delong: Pyrazomycin — a Novel Carbon-Linked Nucleoside. 158th National Meeting, Amer. Chem. Soc., New York (1969), Abstr. MICR. 38.
Gutowski, G. E., M. J. Sweeney, D. C. Delong, R. L. Hamill, K. Gerzon, and R. W. Dyke: Biochemistry and Biological Effects of the Pyrazofurins (Pyrazomycins): Initial Clinical Trial. Ann. New York Acad. Sci. 255, 544 (1975).
Williams, R. H., and M. M. Hoehn: Pyrazomycin and Process for Production thereof. U.S. Pat. 3,802,999, April 9, 1974 to Eli Lilly and Company.
Jones, N. D., and M. O. Chaney: The Crystal Structure of Pyrazomycin, A C- Nucleoside Antiviral Agent. 9th Int. Congr. Crystallogr., Kyoto, Japan, Abstr. S. 48.
de Bernardo, S., and M. Weigele: A Synthesis of the Pyrazomycins. J. Organ. Chem. (USA) 41, 287 (1976).
Ohrui, H., and J. J. Fox: Nucleosides LXXXI. An Approach to the Synthesis of C-C Linked P-D-Ribofuranosyl Nucleosides from 2,3-0-Isopropylidene-5-0-trityl-f3-D- ribofuranosyl Chloride. Tetrahedron Letters 1973, 1951.
katagiri, N., K. Takashima, and T. Kato: A Simple Synthesis of the Pyrazofurins. Chem. Commun. 1982, 664.
de Clercq, E., and P. F. Torrence: Nucleoside Analogs with Selective Antiviral Activity. J. Carbohydr. Nucleosides Nucleotides 5, 187 (1978).
Sweeney, M. J., F. A. Davis, G. E. Gutowski, R. L. Hamill, D. H. Hoffmann, and G. A. poore: Experimental Antitumour Activity of Pyrazomycin. Cancer Res. 33, 2619 (1973).
Cadman, E. C., D. E. Dix, and R. E. Handschumacher: Clinical, Biological, and Biochemical Effects of Pyrazofurin. Cancer Res. 38, 682 (1978).
Rossi, A.: The Clinical Uses of Nucleoside Analogues in Malignant Disease. In: Nucleoside Analogues. Chemistry, Biology, and Medical Applications (R. T. Walker, E. de Clercq, and F. Eckstein), p. 409. NATO Advanced Study Institutes Series. New York and London: Plenum Press. 1979.
Levine, H. L., R. S. Brody, and F. H. Westheimer: Inhibition of Orotidine-5’- phosphate Decarboxylase by l-Phospho-p-D-ribofuranosyl)barbituric Acid, 6- Azauridine S’-Phosphate and Uridine 5’-Phosphate. Biochemistry 19, 4993 (1980).
Shirato, S., J. Nagatsu, M. Shibuya, and Y. Kasukabe: Antibiotic Minimycin. Ger. Pat. 2,043,946, March 25, 1971 to Kaken Chemical Co. Ltd. Chem. Abs. 74, 139557h (1971).
Kusakabe, Y., J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose, and S. Shirato: Minimycin, a New Antibiotic. J. Antibiotics 25, 44 (1972).
De Bernardo, S., and M. Weigele: Synthesis of Oxazinomycin (Minimycin). J. Organ. Chem. (USA) 42, 109 (1977).
Takaoka, K., T. Kuwayama, and A. Aoki: Jap.Pat. 615,332 (1971): cited in ref. 140.
Sakata, K., A. Sakurai, and S. Tamura: Studies on Ezomycins, Antifungal Antibiotics. Part I. L-Cystathionine as a Component of Ezomycins A1 and from a Streptomyces. Agr. Biol. Chem. 37, 697 (1973).
Studies on Ezomycins, Antifungal Antibiotics. Part II. Ezoaminuroic Acid, 3-Amino-3,4-dideoxy-D-/o-hexopyranuroic Acid, as a Constituent of Ezomycins A1 and A2. Tetrahedron Letters 1974, 1533.
Studies on Ezomycins, Antifungal Antibiotics. Part III. Isolation of Novel Antifungal Antibiotics, Ezomycins Al5 A2, Bx and B2. Agr. Biol. Chem. 38, 1883 (1974).
Studies on Ezomycins, Antifungal Antibiotics. Part IV. Structures of Ezomycins Ax and A2. Tetrahedron Letters 1974, 4327.
Studies on Ezomycins, Antifungal Antibiotics. Part V. Degradative Studies on Ezomycins Ax and A2.Agr. Biol. Chem. 39, 885 (1975).
Studies on Ezomycins, Antifungal Antibiotics. Part VI. Structures of Ezomycins B1, B2, C1, C2, D1? and D2. Tetrahedron Letters 1975, 3191.
Studies on Ezomycins, Antifungal Antibiotics. Part VII. Structures of Ezomycins A± and A2. Agr. Biol. Chem. 40, 1993 (1976).
Sakata, K., and J. Uzawa: Studies on Ezomycins, Antifungal Antibiotics. Part VIII. Application of C-13 NMR Spectrometry to the Structural Investigation of the Novel Bicyclic Anhydrooctose Uronic Acid Nucleosides, Constituents of Ezomycins. Agr. Biol. Chem. 41, 413 (1977).
Sakata, K., A. Sakurai, and S. Tamura: Studies on Ezomycins, Antifungal Antibiotics. Part IX. Isolation and Antimicrobial Activities of Ezomycins Bl5 B2, Q, C2, and D2. Agr. Biol. Chem. 41, 2027 (1977).
Sakata, K., J. Uzawa, and A. Sakurai: Studies on Ezomycins, Antifungal Antibiotics. Part XI. Application of Carbon-13 N. m. r. Spectroscopy to the Structural Investigation of Ezomycins. Organic Magnetic Resonance 10, 230 (1977).
Ogawa, T., M. Akatsu, and M. Matsui: Synthesis of a Sugar Occurring in an Antibiotic: Ezoaminuroic Acid, the First Example of a Naturally Occurring 3-Amino-3- deoxyhexuronic Acid. Carbohydrate Research 44, C22 (1975).
Cerny, M., and J. Pacak: Desoxyzucker III. Uber Rtaktionen der 2-0-Tosyl-l,6: 3,4- dianhydro-P-D-galactopyranose Darstellung von 4-Desoxy-D-XF/ohexose (4-Desoxy-D- glucose) und 4-Desoxy-D-tfratoohexose (4-Desoxy-D-altrose). Collect. Czech. Chem. Comm. 27, 94 (1962).
Mieczowski, J., and A. Zamojski: Total Syntheses of Methyl(methyl 3-amino-3,4- dideoxy-oc- and p-DL-/hexopyranoside)uronates. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 23, 581 (1975). [Chem. Abs. 84, 31341a (1976)].
Isono, K., P. F. Crain, and J. A. Mccloskey: Isolation and Structure of Octosyl Acids. Anhydrooctose Uronic Acid Nucleosides. J. Amer. Chem. Soc. 97, 943 (1975).
Anzai, K., and T. Saita: Synthesis of 3,7-Anhydrooctose Derivatives Related to Octosyl Acids. Chem. Commun. 1976, 681.
Anzai, K., and T. Saita: The Synthesis of Several Octose Derivatives Related to Octosyl Acids A and B. B. ll . Chem. Soc. Japan 50, 169 (1977).
Kim, K. S., and W. A. Szarek: Synthesis of S’J’-Anhydrooctose Nucleosides Related to the Ezomycins and the Octosyl Acids. Canad. J. Chem. 59, 878 (1981).
Syntheses Related to the 3,7-Anhydrooctose in the Ezomycins and the Octosyl Acids. Carbohydrate Research 100, 169 (1982).
Buchanan, J. M., and S. C. Hartman: Enzymic Reactions in the Synthesis of the Purines. Adv. Enzymology 21, 199 (1959).
Hartman, S. C.: Purines and Pyrimidines. In: Metabolic Pathways, 3rd Edn., Vol. 4 (D. M. Greenberg, Ed.), p. 1. New York: Academic Press. 1970.
Elstner, E. F., and R. J. Suhadolnik: Nucleoside Antibiotics. Biosynthesis of the Maleimide Nucleoside Antibiotic, Showdomycin, by Streptomyces showdoensis. Biochemistry 10, 3608 (1971).
Nucleoside Antibiotics. Asymmetric Incorporation of Glutamic Acid and Acetate into the Maleimide Ring of Showdomycin by Streptomyces showdoensis. Biochemistry 11, 2578 (1972).
Elstner, E. F., R. J. Suhadolnik, and A. Allerhand: Effect of Changes in the Pool of Acetate on the Incorporation and Distribution of 13 C- and 14C-Labeled Acetate into Showdomycin by Streptomyces showdoensis. J. Biol. Chem. 248, 5385 (1973).
buchaanan, J. G., M. R. Hamblin, and R. H. Wightman: Heriot-Watt University, unpublished results.
Sawa, T., Y. Fukagawa, Y. Shimauchi, K. Ito, M. hamada, T. Takeuchi, and H. Umezawa: Studies on Formycin and Formycin B Phosphates. J. Antibiotics Ser. A 18, 259 (1965).
Ochi, K., S. Yashima, and Y. Eguchi: Biosynthesis of Formycin. Formation of Formycin from Formycin B. J. Antibiotics 28, 965 (1975).
Kunimoto, T., T. Sawa, T. Wakashiro, M. HORI, and H. Umezawa: Biosynthesis of the Formycin Family. J. Antibiotics 24, 253 (1971).
Ochi, K., S. Kikuchi, S. Yashima, and Y. Eguchi: Biosynthesis of Formycin. Incorporation and Distribution of Labeled Compounds into Formycin. J. Antibiotics 29, 638 (1976).
Ochi, K., S. Yashima, Y. Eguchi, and K. Matsushita: Biosynthesis of Formycin. Incorporation and Distribution of 13C-, 14C-, and 15N-Labeled Compounds into Formycin. J. Biol. Chem. 254, 8819 (1979).
Ochi, K., S. Iwamoto, E. Hayase, S. Yashima, and Y. Okami: Biosynthesis of Formycin. Role of Certain Amino Acids in Formycin Biosynthesis. J. Antibiotics 27, 909 (1974).
Krugh, T. R.: Tautomerism of the Nucleoside Antibiotic Formycin, as studied by Carbon-13 Nuclear Magnetic Resonance. J. Amer. Chem. Soc. 95, 4761 (1973).
Suhadolnik, R. J., and N. L. Reichenbach: Glutamate as the Common Precursor for the Aglycon of the Naturally Occurring C-Nucleoside Antibiotics. Biochemistry 20, 7042 (1981).
Isono, K., and R. J. Suhadolnik: The Biosynthesis of the Nucleoside Antibiotics: Minimycin Formation by Streptomyces hygroscopicus. Ann. New York Acad. Sci. 255, 390 (1975).
Biosynthesis of the C-Nucleoside, Minimycin: Asymmetric Incorporation of Glutamate and Acetate into the Oxazine Ring. J. Antibiotics 30, 272 (1977).
Isono, K., T. Sato, K. Hirasawa, S. Funayama, and S. Suzuki: Biosynthesis of the Nucleoside Skeleton of Polyoxins. J. Amer. Chem. Soc. 100, 3937 (1978).
Sato,T., K. Hirasawa, J. Uzawa, T. Inaba, and K. Isono: Biosynthesis of Octosyl Acid A: Incorporation of C-13 Labeled Glucose.Tetrahedron Letters 1979, 3441.
Uematsu, T., and R. J. Suhadolnik: Pseudouridine: Biosynthesis by Strepto-verticillicum Ladakanus. Biochim. Biophys. Acta 319, 348 (1973).
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1983 Springer-Verlag/Wien
About this chapter
Cite this chapter
Buchanan, J.G. (1983). The C-Nucleoside Antibiotics. In: Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 44. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8714-2_4
Download citation
DOI: https://doi.org/10.1007/978-3-7091-8714-2_4
Publisher Name: Springer, Vienna
Print ISBN: 978-3-7091-8716-6
Online ISBN: 978-3-7091-8714-2
eBook Packages: Springer Book Archive