Abstract
Some aminoglycosides of microbial origin are listed in Table 1. Recently derivatives of these antibiotics, which are effective against resistant organisms,
have been developed; some of them are described below. Except these, there are many aminosugar-containing antibiotics, which are usually classified to other groups of antibiotics: macrolide, lincomycin, streptothricin, etc.
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References
Akita, E., T. Tsuruoka, N. Ezaki, and T. Niida: Studies on antibiotic SF-733, a new antibiotic. II. Chemical structure of antibiotic SF-733. J. Antibiotics (Tokyo) 23, 173 (1970).
Arcamone, F., and F. Bizioli: Isolation and constitution of trehalosamine, a new aminosugar from a streptomycetes. Gazz. Chim. Ital. 87, 896 (1957).
Benveniste, R., and J. Davies: R-Factor mediated gentamicin resistance: a new enzyme which modifies aminoglycosidic antibiotics. FEBS Letters 14, 293 (1971 a).
Benveniste, R., and J. Davies: Enzymatic acetylation of aminoglycoside antibiotics by Escherichia coli carrying an R factor. Biochemistry 10, 1787 (1971 b).
Bissel, D. M.: Formation of an altered enzyme by Escherichia coli in the presence of neomycin. J. Mol. Biol. 14, 619 (1965).
Biswas, D. K., and L. Gorini: The attachment site of streptomycin to the 30S ribosomal subunit. Proc. Natl. Acad. Sci. U.S. 69, 2141 (1972).
Bodley, J. W., and E. M. Davie: A study of the mechanism of ambiguous amino acid coding by poly U: the nature of the products. J. Mol. Biol. 18, 344 (1966).
Bollen, A., J. Davies, M. Ozaki, and S. Mizushima: Identification of the ribosomal protein conferring sensitivity to the antibiotic spectinomycin in Escherichia coli. Science 165, 85 (1969 a).
Bollen, A., T. Helser, T. Yamada, and J. Davies: Altered ribosomes in antibiotic-resistant mutants of E. coli. Cold Spring Harbor Symp. Quant. Biol. 34, 95 (1969 b).
Brzezinska, M., R. Benveniste, J. Davies, P. J. L. Daniels, and J. Weinstein: Gentamicin resistance in strains of Pseudomonas aeruginosa mediated by enzymatic N-acetylation of the deoxystreptamine moiety. Biochemistry 11, 761 (1972).
Caskey, C. T.: In: Molecular mechanism of antibiotic action on protein biosynthesis and membranes. Amsterdam: Elsevier Pub. Co. 1972.
Chang, F. N., and J. G. Flaks: Topography of the Escherichia coli 30S ribosomal subunit and streptomycin binding. Proc. Natl. Acad. Sci. U.S. 67, 1321 (1970).
Chang, F. N., and J. G. Flaks: The binding of dihydrostreptomycin to E. coli ribosomes: Characteristics and equilibrium of the reaction. Antimicr. Ag. Chemoth. 2, 294 (1972).
Chang, F. N., and J. G. Flaks: The binding of dihydrostreptomycin to E. coli ribosomes: Kinetics of the reaction. Antimicr. Ag. Chemoth. 2, 308 (1972).
Cooper, D. J., R. S. Jaret, and H. Reimann: Structure of sisomicin, a novel unsaturated aminoglycoside antibiotic from Micromonospora inyoensis. Chem. Commun. 285 (1971).
Cooper, D. J., H. M. Marigliano, M. D. Yudis, and T. Traubel: Recent developments in the chemistry of gentamicin. J. Infect. Diseases 119, 342 (1969).
Davies, J.: Structure-activity relationships among the aminoglycoside antibiotics: Comparison of the neomycins and hybrimycins. Biochim. Biophys. Acta 222, 674 (1970).
Davies, J., M. Brzezinska, and R. Benveniste: R factors: Biochemical mechanisms of resistance to aminoglycoside antibiotics. Ann. N. Y. Acad. Sci. 182, 226 (1971).
Davies, J., and B. D. Davis: Misreading of RNA codewords induced by aminoglycoside antibiotics: the effect of drug concentration. J. Biol. Chem. 243, 3312 (1968).
Davies, J., W. Gilbert, and L. Gorini: Streptomycin, suppression and the code. Proc. Natl. Acad. Sci. U.S. 51, 883 (1964).
Davies, J., L. Gorini, and B. D. Davis: Misreading of RNA codewords induced by aminoglycoside antibiotics. Mol. Pharmacol. 1, 93 (1965).
Davis, B. D.: Use of antibiotics in the study of ribosome action. Antimicr. Ag. Chemoth. 1969, 11.
Del Bene, V. E., and W. E. Farrar, Jr.: Tobramycin: In vitro activity and comparison with kanamycin and gentamicin. Antimicr. Ag. Chemoth. 1, 340 (1972).
Doi, O., S. Kondo, N. Tanaka, and H. Umezawa: Phosphorylating enzyme from Pseudomonas aeruginosa. J. Antibiotics (Tokyo) 22, 273 (1969).
Doi, O., M. Miyamoto, N. Tanaka, and H. Umezawa: Inactivation and phosphorylation of kanamycin by drug-resistant Staphylococcus aureus. Appl. Microbiol. 16, 1282 (1968 a).
Doi, O., M. Ogura, N. Tanaka, and H. Umezawa: Inactivation of kanamycin, neomycin and streptomycin by enzymes obtained in cells of Pseudomonas aeruginosa. Appl. Microbiol. 16, 1276 (1968b).
Dunlap, B. E., K. H. Friderici, and F. Rottman: 2′-O-Methyl polynucleotides as templates for cell-free amino acid incorporation. Biochemistry 10, 2581 (1971).
Funatsu, G., K. Nierhaus, and B. Wittmann-Liebold: Ribosomal proteins. XXII. Studies on the altered protein S5 from a spectinomycin-resistant mutant of Escherichia coli. J. Mol. Biol. 64, 201 (1972).
García-Patrone, M., C. A. Perazzolo, F. Baralle, N. S. González, and I. D. Algranati: Studies on dissociation factor of bacterial ribosomes: Effect of antibiotics. Biochim. Biophys. Acta 246, 291 (1971).
Gorini, L., and E. Kataja: Phenotypic repair by streptomycin of defective genotypes in E. coli. Proc. Natl. Acad. Sci. U.S. 51, 487 (1964).
Gurgo, C., D. Apirion, and D. Schlessinger: Polyribosome metabolism in Escherichia coli treated with chloramphenicol, neomycin, spectinomycin or tetracycline. J. Mol. Biol. 45, 205 (1969).
Hashimoto, K.: Streptomycin resistance in Escherichia coli analyzed by transduction. Genetics 45, 49 (1960).
Hatfield, D.: Oligonucleotide-ribosome-AA-sRNA interactions. Cold Spring Harbor Symp. Quant. Biol. 34, 619 (1966).
Helser, T. L., J. E. Davies, and J. E. Dahlberg: Change in methylation of 16S ribosomal RNA associated with mutation to kasugamycin resistance in Escherichia coli. Nature New Biol. 233, 12 (1971).
Helser, T. L., J. E. Davies, and J. E. Dahlberg: Mechanism of kasugamycin resistance in Escherichia coli. Nature New Biol. 235, 6 (1972).
Herr, R. R., T. E. Eble, M. E. Bergy, and H. K. Janke: Isolation and characterization of streptozotocin. Antibiot. Ann. 1959/1960, 236 (1960).
Herr, R. R., H. K. Janke, and A. D. Argoudelis: The structure of streptozotocin. J. Am. Chem. Soc. 89, 4808 (1967).
Herzog, A.: An effect of streptomycin on the dissociation of Escherichia coli 70S ribosomes. Biochem. Biophys. Res. Commun. 15, 172 (1964).
Herzog, A., A. Ghysen, and A. Bollen: Sensitivity and resistance to streptomycin in relation with factor-mediated dissociation of ribosomes. FEBS Letters 15, 291 (1971).
Hichens, M., and K. L. Rinehart: Chemistry of the neomycins. XII. The absolute configuration of deoxystreptamine in the neomycins, paromomycins and kanamycins. J. Am. Chem. Soc. 85, 1547 (1963).
Hoeksema, H., A. D. Argoudelis, and P. F. Wiley: Chemistry of actinospectacin II. The structure of actinospectacin. J. Am. Chem. Soc. 84, 3212 (1962).
Holland, J. J., C. A. Buck, and B. J. MaCarthy: Stimulation of protein synthesis in vitro by partially degraded ribosomal ribonucleic acid and transfer ribonucleic acid. Biochemistry 5, 358 (1966).
Horii, S., and Y. Kameda: Structure of the antibiotic validamycin A. J. C. S. Chem. Commun. 747 (1972).
Inoue, S., T. Tsuruoka, and T. Niida: The structure of nojirimycin, a piperidinose sugar antibiotic. J. Antibiotics (Tokyo), Ser. A 19, 288 (1966).
Ishida, N., K. Kumagai, T. Niida, K. Hamamoto, and T. Shomura: Nojirimycin, a new antibiotic. I. Taxonomy and fermentation. J. Antibiotics (Tokyo), Ser. A 20, 62 (1967).
Ishida, N., K. Kumagai, T. Niida, T. Tsuruoka, and H. Yumoto: Nojirimycin, a new antibiotic. II. Isolation, characterization and biological activity. J. Antibiotics (Tokyo), Ser. A 20, 66 (1967).
Kaji, H., and A. Kaji: Specific binding of sRNA to ribosomes: effect of streptomycin. Proc. Natl. Acad. Sci. U.S. 54, 213 (1965).
Kaji, H., and Y. Tanaka: Binding of dihydrostreptomycin to ribosomal subunits. J. Mol. Biol. 32, 221 (1968).
Kawabe, H., F. Kobayashi, M. Yamaguchi, R. Utahara, and S. Mitsuhashi: 3″-Phosphoryldihydrostreptomycin produced by the inactivating enzyme of Pseudomonas aeruginosa. J. Antibiotics (Tokyo), 24, 651 (1971).
Kawaguchi, H., T. Naito, S. Nakagawa, and K. Fujisawa: BB-K8, a new semisynthetic aminoglycoside antibiotic. J. Antibiotics (Tokyo) 25, 695 (1972).
Kobayashi, F., M. Yamaguchi, and S. Mitsuhashi: Activity of lividomycin against Pseudomonas aeruginosa: Its inactivation by phosphorylation induced by resistant strain. Antimicr. Ag. Chemoth. 1, 17 (1972).
Koch, K. F., and J. A. Rhodes: Structure of nebramycin factor 6, a new aminoglycosidic antibiotic. Antimicr. Ag. Chemoth. 1970, 313 (1971).
Kogut, M., and E. Prizant: Effects of dihydrostreptomycin treatment in vivo on the ribosome cycle in Escherichia coli. FEBS Letters 12, 17 (1970).
Kondo, S., E. Akita, and M. Koike: The structure of destomycin A.J. Antibiotics (Tokyo), Ser. A 19, 139 (1966).
Kondo, S., M. Okanishi, R. Utahara, K. Maeda, and H. Umezawa: Isolation of kanamycin and paromamine inactivated by E. coli carrying R factor. J. Antibiotics (Tokyo) 21, 22 (1968).
Kondo, S., M. Sezaki, M. Koike, M. Shimura, E. Akita, K. Satoh, and T. Hara: Destomycins A and B, two new antibiotics produced by a Streptomyces. J. Antibiotics (Tokyo), Ser. A 18, 38 (1965).
Kondo, S., H. Yamamoto, H. Naganawa, H. Umezawa, and S. Mitsuhashi: Isolation and characterization of lividomycin A inactivated by Pseudomonas aeruginosa and Escherichia coli carrying R factor. J. Antibiotics (Tokyo) 25, 483 (1972).
Koyama, G., Y. Iitaka, K. Maeda, and H. Umezawa: The crystal structure of kanamycin. Tetrahedron Letters 1968, 1875.
Kozak, M. and D. Nathans: Differential inhibition of coliphage MS2 protein synthesis by ribosome-directed antibiotics. J. Mol. Biol. 70, 41 (1972).
Kreider, G., and B. L. Brownstein: A mutation suppressing streptomycin dependence II: An altered protein on the 30S ribosomal subunit. J. Mol. Biol. 61, 135 (1971).
Kreider, G., and B. L. Brownstein: Ribosomal proteins involved in the suppression of streptomycin dependence in Escherichia coli. J. Bacteriol. 109, 780 (1972).
Lelong, J. C., M. A. Cousin, D. Gros, M. Grunberg-Manago, and F. Gros: Streptomycin induced release of fMet-tRNA from the ribosomal initiation complex. Biochem. Biophys. Res. Commun. 42, 530 (1971).
Lennette, E. T., and D. Apirion: The level of f-Met-tRNA on ribosomes from streptomycin treated cells. Biochem. Biophys. Res. Commun. 41, 804 (1970).
Leon, S. A., and T. D. Brock: Effect of streptomycin and neomycin on physical properties of the ribosome. J. Mol. Biol. 24, 391 (1967).
Likover, T. E. and C. G. Kurland: The contribution of DNA to translation errors induced by streptomycin in vitro. Proc. Natl. Acad. Sci. U.S. 58, 2385 (1967).
Likover, T. E., and C. G. Kurland: Ribosomes from a streptomycin-dependent strain of Escherichia coli J. Mol. Biol. 25, 497 (1967).
Lin, Y., and N. Tanaka: Mechanism of bottromycin action in polypeptide biosynthesis. J. Biochem. (Tokyo) 63, 1 (1968).
Luzzatto, L., D. Apirion, and D. Schlessinger: Mechanism of action of streptomycin in E. coli: interruption of the ribosome cycle at the initiation of protein synthesis. Proc. Natl. Acad. Sci. U.S. 60, 873 (1968).
Luzzatto, L., D. Apirion, and D. Schlessinger: Streptomycin action: Greater inhibition of Escherichia coli ribosome function with exogenous than with endogenous messenger ribonucleic acid. J. Bacteriol. 99, 206 (1969a).
Luzzatto, L., D. Apirion, and D. Schlessinger: Polyribosome depletion and blockage of the ribosome cycle by streptomycin in Escherichia coli. J. Mol. Biol. 42, 315 (1969 b).
Machiyama, N.: Mechanism of action of lividomycin, a new aminoglycosidic antibiotic. J. Antibiotics (Tokyo) 24, 706 (1971).
Maehr, H., and C. P. Schaffner: Chemistry of the gentamicins. II. Stereochemistry and synthesis of gentosamine. Total structure of gentamicin A. J. Am. Chem. Soc. 92, 1697 (1970).
Mason, D. J., A. Dietz, and R. M. Smith: Actinospectacin, a new antibiotic. I. Discovery and biological properties. Antibiot. & Chemotherapy 11, 118 (1961).
Masukawa, H.: Localization of sensitivity to kanamycin and streptomycin in 30 S ribosomal proteins of Escherichia coli. J. Antibiotics (Tokyo) 22, 612 (1969).
Masukawa, H., and N. Tanaka: Stimulation by aminoglycosidic antibiotics of DNA-directed protein synthesis. J. Biochem. (Tokyo) 62, 202 (1966).
Masukawa, H., and N. Tanaka: Miscoding activity of aminosugars. J. Antibiotics (Tokyo), Ser. A 21, 70 (1968).
Masukawa, H., N. Tanaka, and H. Umezawa: Localization of kanamycin sensitivity in the 23 S core of 30 S ribosomes of E. oli. J. Antibiotics (Tokyo), Ser. A 21, 517 (1968).
McCarthy, B. J., and J. J. Holland: Denatured DNA as a direct template for in vitro protein synthesis. Proc. Natl. Acad. Sci. U.S. 54, 880 (1965).
Mitsuhashi, S., F. Kobayashi, and M. Yamaguchi: Enzymatic inactivation of gentamicin C components by cell-free extract from Pseudomonas aeruginosa. J. Antibiotics (Tokyo) 24, 400 (1971).
Mizuno, S., K. Nitta, and H. Umezawa: Mechanism of action of negamycin in E. coli K 12. II. Miscoding activity in polypeptide synthesis directed by synthetic polynucleotide. J. Antibiotics (Tokyo) 23, 589 (1970).
Modolell, J., and B. D. Davis: Breakdown by streptomycin of initiation complexes formed on ribosomes of Escherichia coli. Proc. Natl. Acad. Sci. U.S. 67, 1148 (1970).
Mori, T., T. Ichiyanagi, H. Kondo, K. Tokunaga, T. Oda, and K. Munakata: Studies on new antibiotic lividomycins. II. Isolation and characterization of lividomycins A, B and other aminoglycosidic antibiotics produced by Streptomyces lividus. J. Antibiotics (Tokyo) 24, 339 (1971).
Murase, M., T. Ito, S. Funatsu, and H. Umezawa: Studies on kanamycin related compounds produced during fermentation by mutants of Streptomyces kanamyceticus. Isolation and properties. Progr. Antimicr. Anticancer Chemoth. (Univ. Tokyo Press) 2, 1098 (1970).
Naganawa, H., S. Kondo, K. Maeda, and H. Umezawa: Structure determination of enzymatically phosphorylated products of aminoglycoside antibiotic by proton magnetic resonance. J. Antibiotics (Tokyo) 24, 823 (1971 a).
Naganawa, H., M. Yagisawa, S. Kondo, T. Takeuchi, and H. Umezawa: The structure determination of an enzymatic inactivation product of 3′,4′-dideoxykanamycin B. J. Antibiotics (Tokyo) 24, 913 (1971b).
Neuss, N., K. F. Koch, B. B. Molloy, W. Day, L. L. Huckstep, D. E. Dorman, and J. D. Roberts: Structure of hygromycin B, an antibiotic from Streptomyces hygroscopicus: the use of CMR spectra in structure determination. I. Helv. Chim. Acta 53, 2314 (1970).
Nomura, M., and F. Engbaek: Expression of ribosomal protein genes as analyzed by bacteriophage Mu-induced mutations. Proc. Natl. Acad. Sci. U.S. 69, 1526 (1972).
Oda, T., T. Mori, Y. Kyotani, and M. Nakayama: Studies on new antibiotic lividomycins. IV. Structure of lividomycin A. J. Antibiotics (Tokyo) 24, 511 (1971).
Okamoto, S., and Y. Suzuki: Chloramphenicol-, dihydrostreptomycin-, and kanamycin-inactivating enzymes from multiple drug-resistant Escherichia coli carrying episome “R”. Nature 208, 1301 (1965).
Okanishi, M., S. Kondo, Y. Suzuki, S. Okamoto, and H. Umezawa: Studies on inactivation of kanamycin and resistance of E. coli. J. Antibiotics (Tokyo), Ser. A 20, 132 (1967).
Okanishi, M., S. Kondo, R. Utahara, and H. Umezawa: Phosphorylation and inactivation of aminoglycosidic antibiotics by E. coli carrying R factor. J. Antibiotics (Tokyo) 21, 13 (1968).
Okuyama, A., N. Machiyama, T. Kinoshita, and N. Tanaka: Inhibition by kasugamycin of initiation complex formation on 30S ribosomes. Biochem. Biophys. Res. Commun. 43, 196 (1971).
Okuyama, A., and N. Tanaka: Differential effects of aminoglycosides on cistron-specific initiation of protein synthesis. Biochem. Biophys. Res. Commun. 49, 951 (1972).
Okuyama, A., T. Watanabe, and N. Tanaka: Effects of aminoglycoside antibiotics on initiation of viral RNA-directed protein synthesis. J. Antibiotics (Tokyo) 25, 212 (1972).
Old, D., and L. Gorini: Amino acid changes provoked by streptomycin in a polypeptide synthesized in vitro. Science 150, 1290 (1965).
Oliver, T. J., A. Goldstein, R. R. Bower, J. C. Holper, and R. H. Otto: M-141, a new antibiotic. I. Antimicrobial properties, identity with actinospectacin, and production by Streptomyces flavopersicus, sp. n. Antimicr. Ag. Chemoth. 495 (1961).
Ozaki, M., S. Mizushima, and M. Nomura: Identification and functional characterization of the protein controlled by the streptomycin-resistant locus in E. coli. Nature 226, 333 (1969).
Ozanne, B., R. Benveniste, D. Tipper, and J. Davies: Aminoglycoside antibiotics: inactivation by phosphorylation in E. coli carrying R factor. J. Bacteriol. 100, 1144 (1969).
Pestka, S., R. Marchall, and M. Nirenberg: RNA codewords and protein synthesis. V. Effects of streptomycin on the formation of ribosome-sRNA complexes. Proc. Natl. Acad. Sci. U.S. 53, 639 (1965).
Pestka, S.: Studies on the formation of transfer ribonucleic acid-ribosome complexes. I. The effect of streptomycin and ribosomal dissociation on 14C-aminoacyl transfer ribonucleic acid binding to ribosomes. J. Biol. Chem. 241, 367 (1966).
Petitpas-Dewandre, A., H. Barbason, and W. G. Verly: Affinite pour la streptomycine des ribosomes d’Escherichia coli. Europ. J. Biochem. 7, 307 (1969).
Price, A. R., and F. Rottman: 2′-O-Methyloligoadenylates as templates for the binding of lysyl transfer ribonucleic acid to ribosomes. Biochemistry 9, 4524 (1970).
Price, K. E., D. R. Chisholm, M. Misiek, F. Leitner, and Y. H. Tsai: Microbiological evaluation of BB-K8, a new semisynthetic aminoglycoside. J. Antibiotics (Tokyo) 25, 709 (1972).
Reimann, H., R. S. Jaret, and D. J. Cooper: Sisomicin: Stereochemistry and attachment of the unsaturated sugar moiety. Chem. Commun. 924 (1971).
Rinehart, K. L.: The neomycins and related antibiotics. New York: John Wiley & Sons 1964.
Rinehart, K. L., M. Hichens, A. D. Argoudelis, W. S. Chilton, H. E. Carter, M. P. Georgiadis, C. P. Schaffner, and R. T. Schillings: Chemistry of the neomycins. X. Neomycins B and C. J. Am. Chem. Soc. 84, 3218 (1962).
Schwartz, J. H.: An effect of streptomycin on the biosynthesis of the coat protein of coliphage of f2 by extracts of E. coli. Proc. Natl. Acad. Sci. U.S. 53, 1133 (1965).
Shaw, W. V.: The enzymatic acetylation of chloramphenicol by extracts of R factor-resistant Escherichia coli. J. Biol. Chem. 242, 687 (1967).
Sherman, M. I.: The role of ribosomal conformation in protein biosynthesis. Further studies with streptomycin. Europ. J. Biochem. 25, 291 (1972).
Sherman, M. I., and M. V. Simpson: The role of ribosomal conformation in protein biosynthesis: the streptomycin-ribosome interaction. Proc. Natl. Acad. Sci. U.S. 64, 1388 (1969).
Shibahara, S., S. Kondo, K. Maeda, H. Umezawa, and M. Ohno: The total synthesis of negamycin and the antipode. J. Am. Chem. Soc. 94, 4353 (1972).
Shier, W. T., K. L. Rinehart, Jr., and D. Gottlieb: Preparation of four new antibiotics from a mutant of Streptomyces fradiae. Proc. Natl. Acad. Sci. U.S. 63, 198 (1969).
Shier, W. T., K. L. Rinehart, Jr., and D. Gottlieb: Preparation of two new aminoglycoside antibiotics. J. Antibiotics (Tokyo) 23, 51 (1970).
Shoji, J., S. Kozuki, M. Mayama, Y. Kawamura, and K. Matsumoto: Isolation of a new water-soluble basic antibiotic A-396-I. J. Antibiotics (Tokyo) 23, 291 (1970).
Shoji, J., and Y. Nakagawa: Structural feature of antibiotic A-396-I. J. Antibiotics (Tokyo) 23, 569 (1970).
Shomura, T., N. Ezaki, T. Tsuruoka, T. Niwa, E. Akita, and T. Niida: Studies on antibiotic SF-733, a new antibiotic. I. taxonomy, isolation and characterization. J. Antibiotics (Tokyo) 23, 155 (1970).
Sparling, P. F.: Kasugamycin resistance: 30S ribosomal mutation with an unusual location on the Escherichia coli chromosome. Science 167, 56 (1968).
Suhara, Y., K. Maeda, H. Umezawa, and M. Ohno: Chemical studies on kasugamycin. V. The structure of kasugamycin. Tetrahedron Letters 1966, 1239.
Suzuki, Y., M. Hori, and H. Umezawa: Effect of antibiotics on magnesium ion removal from E. coli ribosome suspensions. J. Antibiotics (Tokyo) 21, 571 (1968).
Suzuki, Y., and S. Okamoto: The enzymatic acetylation of chloramphenicol by the multiple drug-resistant Escherichia coli carrying R factor. J. Biol. Chem. 242, 4722 (1967).
Takasawa, S., R. Utahara, M. Okanishi, K. Maeda, and H. Umezwa: Studies on adenylstreptomycin, a product of streptomycin inactivation by E. coli carrying R factor. J. Antibiotics (Tokyo) 21, 477 (1968).
Tanaka, N., and S. Igusa: Effects of viomycin and polymyxin B on protein synthesis in vitro. J. Antibiotics (Tokyo) 21, 239 (1968).
Tanaka, N., H. Masukawa, and H. Umezawa: Structural basis of kanamycin for miscoding activity. Biochem. Biophys. Res. Commun. 26, 544 (1967 a).
Tanaka, N., T. Nishimura, H. Yamaguchi, C. Yamamoto, Y. Yoshida, K. Sashikata, and H. Umezawa: Mechanism of action of kasugamycin. J. Antibiotics (Tokyo) 17, 140 (1965).
Tanaka, N., K. Sashikata, T. Nishimura, and H. Umezawa: Activity of ribosomes from kanamycin-resistant E. coli. Biochem. Biophys. Res. Commun. 16, 216 (1964).
Tanaka, N., K. Sashikata, and H. Umezawa: Antibiotic-sensitivity of ribosomes from kanamycin-resistant E. coli. J. Antibiotics, (Tokyo), Ser. A 20, 115 (1967b).
Tanaka, N., K. Sashikata, H. Yamaguchi, and H. Umezawa: Inhibition of protein synthesis by bottromycin A2 and its hydrazide. J. Biochem. (Tokyo) 60, 405 (1966 a).
Tanaka, N., H. Yamaguchi, and H. Umezawa: Mechanism of kasugamycin action on polypeptide synthesis. J. Biochem. (Tokyo) 60, 429 (1966b).
Tanaka, N., Y. Yoshida, K. Sashikata, H. Yamaguchi, and H. Umezawa: Inhibition of polypeptide synthesis by kasugamycin, an aminoglycoside antibiotic. J. Antibiotics (Tokyo) 19, 65 (1966 c).
Tanaka, Y., and H. Kaji: The role of ribosomal protein for the binding of dihydrostreptomycin to ribosomes. Biochem. Biophys. Res. Commun. 32, 313 (1968).
Traub, P., K. Hosokawa, and M. Nomura: Streptomycin sensitivity and the structural components of the 30S ribosomes of Escherichia coli. J. Mol. Biol. 19, 211 (1966).
Uehara, Y., S. Kondo, H. Umezawa, K. Suzukake, and M. Hori: Negamycin, a miscoding antibiotic with a unique structure. J. Antibiotics (Tokyo) 25, 685 (1972).
Umezawa, H.: Recent advances in chemistry and biochemistry of antibiotics. Microbial Chemistry Research Foundation (1964).
Umezawa, H., O. Doi, M. Ogura, S. Kondo, and N. Tanaka: Phosphorylation and inactivation of kanamycin by Pseudomonas aeruginosa. J. Antibiotics (Tokyo), Ser. A 21, 154 (1968a).
Umezawa, H., Y. Nishimura, T. Tsuchiya, and S. Umezawa: Syntheses of 6′-N-methylkanamycin and 3′,4′-dideoxy-6′-N-methylkanamycin B active against resistant strains having 6′-N-acetylating enzymes. J. Antibiotics (Tokyo) 25, 743 (1972 a).
Umezawa, H., Y. Okami, T. Hashimoto, Y. Suhara, M. Hamada, and T. Takeuchi: A new antibiotic, kasugamycin. J. Antibiotics (Tokyo), Ser. A 18, 101 (1965).
Umezawa, H., M. Okanishi, S. Kondo, K. Hamana, R. Utahara, K. Maeda, and S. Mitsuhashi: Phosphorylative inactivation of aminoglycosidic.antibiotics by Escherichia coli carrying R factor. Science 157, 1559 (1967 a).
Umezawa, H., M. Okanishi, R. Utahara, K. Maeda, and S. Kondo: Isolation and structure of kanamycin inactivated by a cell-free system of kanamycin-resistant E. coli. J. Antibiotics (Tokyo), Ser. A 20, 136 (1967b).
Umezawa, H., S. Takasawa, M. Okanishi, and R. Utahara: Adenylstreptomycin, a product of streptomycin inactivated by E. coli carrying R factor. J. Antibiotics (Tokyo), Ser. A 21, 81 (1968b).
Umezawa, H., M. Ueda, K. Maeda, K. Yagishita, S. Kondo,Y. Okami, R. Utahara, Y. Osato, K. Nitta, and T. Takeuchi: Production and isolation of a new antibiotic, kanamycin. J. Antibiotics (Tokyo), Ser. A 10, 181 (1957).
Umezawa, H., S. Umezawa, T. Tsuchiya, and Y. Okazaki: 3′,4′-Dideoxykanamycin B active against kanamycin-resistant Escherichia coli and Pseudomonas aeruginosa. J. Antibiotics (Tokyo) 24, 485 (1971 a).
Umezawa, H., H. Yamamoto, M., Yagisawa, S. Kondo, T. Takeuchi, and Y. A. Chabbert: Kanamycin phosphotransferase I: Mechanism of cross-resistance between kanamycin and lividomycin. J. Antibiotics (Tokyo) 26, 407 (1973).
Umezawa, S., T. Tsuchiya, R. Muto, Y. Nishimoto, and H. Umezawa: Synthesis of 3′-deoxykanamycin effective against kanamycin-resistant Escherichia coli and Pseudomonas aeruginosa. J. Antibiotics (Tokyo) 24, 274 (1971 b).
Umezawa, S., T. Tsuchiya, D. Ikeda, and H. Umezawa: Syntheses of 3′,4′-dideoxy- and 3′,4′,5″-trideoxy-ribostamycin active against kanamycin-resistant Escherichia coli and Pseudomonas aeruginosa. J. Antibiotics (Tokyo) 25, 613 (1972 b).
Umezawa, S., K. Umino, S. Shibahara, M. Hamada, and S. Omoto: Fermentation of 3-amino-3-deoxy-d-glucose. J. Antibiotics (Tokyo), Ser. A 20, 355 (1967c).
Umezawa, S., I. Watanabe, T. Tsuchiya, H. Umezawa, and M. Hamada: Synthesis of 5″-deoxylividomycin B. J. Antibiotics (Tokyo) 25, 617 (1972 c).
Uramoto, M., N. Otake, and H. Yonehara: Mannosyl glucosaminide, a new antibiotic. J. Antibiotics (Tokyo), Ser. A 20, 236 (1967).
Vavra, J. J., C. Deboer, A. Dietz, L. J. Hannka, and W. T. Sokolski: Streptozotocin, a new antibacterial antibiotic. Antibiot. Ann. 1959/1960, 230 (1960).
Vogel, Z., T. Vogel, A. Zamir, and D. Elson: Ribosome activation and the binding of dihydrostreptomycin: effect of polynucleotides and temperature on activation. J. Mol. Biol. 54, 379 (1970).
Wallace, B. J., P.-C. Tai, and B. D. Davis: Effect of streptomycin on the response of Escherichia coli ribosomes to the dissociation factor. J. Mol. Biol. (in press).
Weinstein, W. J., G. M. Luedemann, E. M. Oden, G. H. Wagman, J. R. Rosselet, J. A. Marquez, C. T. Coniglio, W. Charney, H. L. Herzog, and J. Black: Gentamicin, a new antibiotic complex from Micromonospora. J. Med. Chem. 6, 463 (1963).
Weinstein, M. J., J. A. Marquez, R. T. Testa, G. H. Wagman, E. M. Oden, and J. A. Waitz: Antibiotic 6640, a new Micromonospora-Produced aminoglycoside antibiotic. J. Antibiotics (Tokyo) 23, 551 (1970).
White, J. R., and H. L. White: Streptomycinoid antibiotics: synergism by puromycin. Science 146, 772 (1964).
Wolfe, A. D., and F. E. Hahn: Stability of ribosomes from streptomycin exposed Escherichia coli. Biochem. Biophys. Res. Commun. 31, 945 (1968).
Woo, P. W. K., H. W. Dion, and Q. R. Bartz: Butirosins A and B, aminoglycoside antibiotics. III. Structures. Tetrahedron Letters 28, 2625 (1971).
Yagisawa, M., H. Naganawa, S. Kondo, M. Hamada, T. Takeuchi, and H. Umezawa: Adenyldideoxykanamycin B, a product of the inactivation of dideoxykanamycin B by Escherichia coli carrying R factor. J. Antibiotics (Tokyo) 24, 911 (1971).
Yagisawa, M., H. Naganawa, S. Kondo, T. Takeuchi, and H. Umezawa: Inactivation of 3′,4′-dedeoxykanamycin B by an enzyme solution of resistant E. coli and isolation of 3′,4′-dideoxykanamycin B 2″-guanylate and 2″-inosinate. J. Antibiotics (Tokyo) 25, 492 (1972 a).
Yagisawa, M., H. Naganawa, S. Kondo, T. Takeuchi, and H. Umezawa: 6′-N-Acetylation of 3′,4′-dideoxykanamycin B by an enzyme in a resistant strain of Pseudomonas aeruginosa. J. Antibiotics (Tokyo) 25, 495 (1972b).
Yagisawa, M., H. Yamamoto, H. Naganawa, S. Kondo, T. Takeuchi, and H. Umezawa: A new enzyme in Escherichia coli carrying R-factor phosphorylating 3′-hydroxyl of butirosin A, kanamycin, neamine and ribostamycin. J. Antibiotics (Tokyo) 25, 748 (1972c).
Yamada, T., K. Kvitek, and J. Davies: The binding of streptomycin and R-factor-inactivated streptomycin to ribosomes. Prog. Antimicr. Anticancer Chemoth. (Univ. Tokyo Press) 2, 562 (1970).
Yamaki, H., and N. Tanaka: Effects of protein synthesis inhibitors on the lethal action of kanamycin and streptomycin. J. Antibiotics (Tokyo), Ser. A 16, 222 (1963).
Yamamoto, H., S. Kondo, K. Maeda, and H. Umezawa: Synthesis of lividomycin A 5″-phosphate, an enzymatically inactivated lividomycin A. J. Antibiotics (Tokyo) 25, 485 (1972 a).
Yamamoto, H., S. Kondo, M. Maeda, and H. Umezawa: Syntheses of 5″-deoxylividomycin A and its amino derivative. J. Antibiotics (Tokyo) 25, 487 (1972 b).
Yamamoto, H., M. Yagisawa, H. Naganawa, S. Kondo, T. Takeuchi, and H. Umezawa: Kanamycin 6′-acetate and ribostamycin 6′-acetate, enzymatically inactivated products by Pseudomonas aeruginosa. J. Antibiotics (Tokyo) 25, 746 (1972c).
Zagorska, L., J. Dondon, J.C. Lelong, F. Gros, and M. Grunberg-Manago: Decoding site of initiator transfer RNA. Biochemie 53, 63 (1971).
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Tanaka, N. (1975). Aminoglycoside Antibiotics. In: Corcoran, J.W., Hahn, F.E., Snell, J.F., Arora, K.L. (eds) Mechanism of Action of Antimicrobial and Antitumor Agents. Antibiotics, vol 3. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46304-4_23
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