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Discovery, chemistry, and chemical biology of microbial products [abstract]
Splendid gifts: Fifth edition
Splendid gifts from microorganisms - the achievements of Satoshi Omura and collaborators. [how to order]
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Publications: 1975-1979
87) K. Atsumi, R. Oiwa, and S. Ōmura: Production of bacillin by Bacillus sp. strain No. KM-208 and its identity with tetaine (bacilysin). J. Antibiot., 28, 77-78 (1975).
88) S. Ōmura and A. Nakagawa: Chemical and biological studies on 16-membered macrolide antibiotics. J. Antibiot., 28, 401-433 (1975).
89) S. Ōmura, Y. Suzuki, C. Kitao, Y. Takahashi, and Y. Konda: Isolation of a new sulfur containing basic substance from a Thermoactinomyces species. J. Antibiot., 28, 609-610 (1975).
90) S. Ōmura, A. Nakagawa, A. Neszmelyi, S. D. Gero, A.-M. Sepulchre, F. Piriou, and G. Lukacs: Carbon-13 nuclear magnetic resonance spectral analysis of 16-membered macrolide antibiotics. J. Am. Chem. Soc., 97, 4001-4009 (1975).
91) S. Ōmura, N. Neszmelyi, M. Sangara, and G. Lukacs: Conformational homogeneity in solution of 14-membered macrolide antibiotics as evidence by 13C NMR spectroscopy. Tetrahedron Lett., 1975, 2939-2942, (1975).
92) S. Ōmura: Advanced studies on 16-membered macrolide antibiotics (Review article). In "Proceedings of the First Intersectional Congress of IAMS" 3, 408-507 (1974).
93) J. Awaya, T. Kesado, and S. Ōmura: Preparation of 13C- and 3H-labeled cerulenin and biosynthesis with 13C NMR. J. Antibiot., 28, 824-827 (1975).
94) R. Oiwa, M. Katagiri, N. Tanaka, Y. Takahashi, K. Satoh, R. Masuma, and S. Ōmura: A new peptide antibiotic KM-8. J. Antibiotics, 28, 819-820 (1975).
95) M. Onda, Y. Konda, Y. Narimatsu, H. Tanaka, J. Awaya, and S. Ōmura: Revised structure for an alkaloid from Streptomyces sp. NA-337. Chem. Pharm. Bull., 23, 2462-2463 (1975).
96) H. Tanaka, Y. Koyama, J. Awaya, H. Marumo, R. Oiwa, M. Katagiri, T. Nagai, and S. Ōmura: Nanaomycins, new antibiotics produced by a strain of Streptomyces. I. Taxonomy, isolation, characterization and biological properties. J. Antibiot., 28, 860-867 (1975).
97) H. Tanaka, Y. Koyama, T. Nagai, H. Marumo, and S. Ōmura: Nanaomycins, new antibiotics produced by a strain of Streptomyces. II. Structure and biosynthesis. J. Antibiot., 28, 868-875 (1975).
98) J. Awaya, T. Ohno, H. Ohno, and S. Ōmura: Substitution of cellular fatty acids in yeast cells by the antibiotic cerulenin and exogenous fatty acids. Biochim. Biophys. Acta, 409, 267-273 (1975).
99) S. Ōmura, A. Nakagawa, H. Takeshima, J. Miyazawa, and C. Kitao: A 13C nuclear magnetic resonance study of the biosynthesis of the 16-membered macrolide antibiotic tylosin. Tetrahedron Lett., 1975, 4503-4506 (1975).
100) H. Tanaka, H. Marumo, T. Nagai, M. Okada, K. Taniguchi, and S. Ōmura: Nanaomycins, new antibiotics produced by a strain of Streptomyces. III. A new component, nanaomycin C, and biological activities of nanaomycin derivatives. J. Antibiotics, 28, 925-930 (1975).
101) S. Ōmura, A. Nakagawa, H. Takeshima, K. Atsumi, J. Miyazawa, F. Piriou, and G. Lukacs: Biosynthetic studies using 13C enriched precursors on the 16-membered macrolide antibiotic leucomycin A3. J. Am. Chem. Soc., 97, 6600-6602 (1975).
102) H. Ohno, T. Ohno, J. Awaya, and S. Ōmura: Inhibition of 6-methylsalicylic acid synthesis by the antibiotic cerulenin. J. Biochem., 78, 1149-1152 (1975).
103) A. Neszmelyi, S. Ōmura, and G. Lukacs: Carbon-13 spin-lattice relaxation times and their use for spectral analysis of 16-membered macrolide antibiotics. J. Chem. Soc., Chem. Commun., 1976, 97-98, (1976)
104) Y. Konda, Y. Suzuki, S. Ōmura, and M. Onda: Alkaloid from Thermoactinomyces species. Chem. Pharm. Bull., 24, 92-96 (1976).
105) T. Ohno, J. Awaya, and S. Ōmura: Inhibition of sporulation by cerulenin and its reversion by exogenous fatty acids in Saccharomyces cerevisiae. Antimicrob. Agents Chemother., 9, 42-48 (1976).
106) J. L. Schwartz, M. Tishler, B. H. Arison, H. M. Safer, and S. Ōmura: Identification of mycolutein and pulvomycin as aureothin and labilomycin, respectively. J. Antibiot., 29, 236-241 (1976).
107) S. Ōmura, H. Takeshima, A. Nakagawa, and J. Miyazawa: The biosynthesis of picromycin using 13C enriched precursors. J. Antibiot., 29, 316-317 (1976).
108) S. Ōmura, T. Nishikiori, R. Oiwa, Y. Iwai, R. Masuma, and M. Katagiri: A new antibiotic KM-214 produced by a strain of Bacillus. J. Antibiot., 29, 477-478 (1976).
109) S. Ōmura, H. Tanaka, Y. Okada, and H. Marumo: Isolation and structure of nanaomycin D, an enantiomer of the antibiotic kalafungin. J. Chem. Soc., Chem. Commun., 1976, 320-321 (1976).
110) S. Ōmura, Y. Iwai, Y. Suzuki, J. Awaya, Y. Konda, and M. Onda: Production of quinoline-2-methanol and quinoline-2-methanol acetate by a new species of Kitasatoa, Kitasatoa griseophaeus. J. Antibiot., 29, 797-803 (1976).
111) A. Nakagawa, K. Suzuki, K. Iwasaki, K. Kaji, S. Ōmura, A. Jakubowski, and M. Tishler: Chemistry of leucomycins. XII. Application of the modified Polonovski reaction to leucomycin A3 N-oxide. Chem. Pharm. Bull., 24, 1749-1756 (1976).
112) S. Ōmura, C. Kitao, H. Tanaka, R. Oiwa, Y. Takahashi, A. Nakagawa, M. Shimada, and Y. Iwai: A new antibiotic, asukamycin, produced by Streptomyces. J. Antibiot., 29, 876-881 (1976).
113) K. Ajisaka, H. Takeshima, and S. Ōmura: Application in biosynthetic studies of 13C isotope shifts in infrared spectroscopy. J. Chem. Soc., Chem. Commun., 1976, 571-572 (1976).
114) T. Miyazaki, H. Yamada, J. Awaya, and S. Ōmura: Isolation and structure of an extracellular polysaccharide from Streptomyces sp. FERM-P1185. J. Gen. Microbiol., 95, 31-38 (1976).
115) S. Ōmura, J. Miyazawa, H. Takeshima, C. Kitao, K. Atsumi, and M. Aizawa: Bioconversion of leucomycins and its regulation by butyrate in a producing strain. J. Antibiot., 29, 1131-1133 (1976).
116) I. Umezawa, K. Komiyama, H. Takeshima, J. Awaya, and S. Omura: A new antitumor antibiotic, PO-357. J. Antibiot., 29, 1249-1251 (1976).
117) T. Hata, S. Nomura, T. Horiuchi, and S. Ōmura: Mode of action of cerulenin on Candida and Saccharomyces. (Review article). In "Proceedings of the Second International Specialized Symposium on Yeast, Tokyo" (Ed. by K. Iwata) 323-332, University of Tokyo Press (1972).
118) S. Ōmura, H. Tanaka, M. Shinohara, R. Oiwa, and T. Hata: Inhibition of bacterial cell wall synthesis amphomycin (Review article). In "Chemotherapy" (Eds. by J. D. Williams and A. M. Geddes) 5, 365-360, Plenum Publishing Co. (1976).
119) S. Ōmura: The antibiotic cerulenin, a novel tool for biochemistry as an inhibitor of fatty acid synthesis. Bacteriol. Rev., 40, 681-697 (1976).
120) S. Ōmura, H. Imai, H. Takeshima, and A. Nakagawa: Structure of a new antimicrobial unsaturated fatty acid from Sm. kitasatoensis NU-23-1. Chem. Pharm. Bull., 24, 3139-3143 (1976).
121) A. Ducruix, C. Pascard, A. Nakagawa, and S. Ōmura: Crystal and molecular structure of diacetyl-3,6-bicyclo-leuconolide A3. J. Chem. Soc., Chem. Commun., 1976, 947-948 (1976).
122) S. Ōmura, J. Miyazawa, H. Takeshima, and C. Kitao: Induction of the bioconversion of leucomycins by glucose in a producing strain. J. Antibiot., 30, 192-193 (1977).
123) S. Ōmura, H. Takeshima, A. Nakagawa, N. Kanemoto, and G. Lukacs: Studies on carboxylic acid metabolism in a macrolide-producing microorganisms using carbon-13 magnetic resonance. Bioorg. Chem., 5, 451-454 (1976).
124) A. Neszmelyi, S. Ōmura, T. T. Thang, and G. Lukacs: A carbon-13 spin-lattice relaxation time study of 14-membered macrolide antibiotics. Tetrahedron Lett., 1977, 725-728 (1977).
125) S. Ōmura: Cerulenin. (Review article) Pharmacia, 13, 109-112 (1977).
126) M. Shimada, H. Honda, J. Awaya, and S. Ōmura: A new antibiotic, OS-1804. J. Antibiot., 30, 330-331 (1977).
127) S. Ōmura, Y. Iwai, A. Hirano, A. Nakagawa, J. Awaya, H. Tsuchiya, Y. Takahashi, and R. Masuma: A new alkaloid AM-2282 of Streptomyces origin. Fermentation, isolation and preliminary characterization. J. Antibiot., 30, 275-282 (1977).
128) S. Ōmura, A. Nakagawa, M. Machida, and H. Imai: Evidence for configurational identity between leucomycin and tylosin. Tetrahedron Lett., 1977, 1045-1048 (1977).
129) H. Takeshima, C. Kitao, and S. Ōmura: Inhibition of the biosynthesis of leucomycin, a macrolide antibiotic, by cerulenin. J. Biochem., 81, 1127-1132 (1977).
130) H. Tanaka, Y. Iwai, R. Oiwa, S. Shinohara, S. Shimizu, T. Oka, and S. Ōmura: Studies on bacterial cell wall inhibitors. II. Inhibition of peptidoglycan synthesis in vivo and in vitro by amphomycin. Biochim. Biophys. Acta, 497, 633-640 (1977).
131) Y. Iwai, H. Tanaka, R. Oiwa, S. Shimizu and S. Ōmura: Studies on bacterial cell wall inhibitors. III. 3-Amino-3-deoxy-D-glucose, an inhibitor of bacterial cell wall synthesis. Biochim. Biophys. Acta, 498, 223-228 (1977).
132) S. Ōmura, A. Nakagawa, H. Sakakibara, O. Okekawa, R. Brandsch, and S. Pestka: Structure-activity relationships among the O-acyl derivatives of leucomycin. Correlation of minimal inhibitory concentrations with binding to Escherichia coli ribosomes. J. Med. Chem., 20, 732-736 (1977).
133) S. Ōmura, H. Takeshima, A. Nakagawa, J. Miyazawa, F. Piriou, and G. Lukacs: Studies on the biosynthesis of 16-membered macrolide antibiotics using carbon-13 nuclear magnetic resonance spectroscopy. Biochemistry, 16, 2860-2866 (1977).
134) S. Ōmura and H. Takeshima: Studies on the biosynthesis of macrolide antibiotics (Review article). Kagaku to Seibutsu, 15, 309-453 (1977).
135) S. Ōmura, Y. Iwai, A. Hirano, J. Awaya, Y. Suzuki, and K. Matsumoto: A new antibiotic, AM-2504. Agricult. Biol. Chem., 41, 1827-1828 (1977).
136) A. Ducruix, C. Pascard, S. Ōmura and A. Nakagawa: 5,9-Diacetyl(3,6)-bicycloleuconolide A3. Acta Cryst. B33, 2314-2316 (1977).
137) M. D. Greenspan, R. C. Macknow, and S. Ōmura: The effect of cerulenin on sterol biosynthesis in Saccharomyces. Lipids, 12, 729-731 (1977).
138) S. Ōmura, H. Tanaka, R. Oiwa, J. Awaya, R. Masuma, and K. Tanaka: New antitumor antibiotics, OS-4742 A1, A2, B1 and B2 produced by a strain of Streptomyces. J. Antibiot., 30, 908-916 (1977).
139) T. T. Thang, G. Lukacs, S. Ōmura, P. Bartner, D. L. Boxler, R. Brambilla, A. K. Mallams, J. B. Morton, P. Reichert, F. D. Sancilio. H. Surprenant, and G. Tomalesky: Megalomicins. 6. Tertiary glycosidic macrolide antibiotics. A structural revision by carbon-13 nuclear magnetic resonance and X-ray crystallography. J. Am. Chem. Soc., 100, 663-666 (1978).
140) Y. Iwai, K. Kumano, and S. Ōmura: Biosynthetic studies of microbial alkaloid pyrindicin using C-13 labelled precursors. Chem. Pharm. Bull., 26, 736-739 (1978).
141) S. Ōmura, C. Kitao, J. Miyazawa, H. Imai, and H. Takeshima: Bioconversion and biosynthesis of 16-membered macrolide antibiotic, tylosin, using enzyme inhibitor: cerulenin. J. Antibiot., 31, 254-256 (1978).
142) Y. Iwai, A. Hirano, J. Awaya, S. Matsuo, and S. Ōmura: 1,3-Diphenethylurea from Streptomyces sp. No. AM-2948. J. Antibiot., 31, 375-376 (1978).
143) T. Nishikiori, R. Masuma, R. Oiwa, M. Katagiri, J. Awaya, Y. Iwai, and S. Ōmura: Aurantinin, a new antibiotic of bacterial origin. J. Antibiot., 31, 525-532 (1978).
144) S. Ōmura, H. Ohno, T. Saheki, M. Yoshida, and A. Nakagawa: Elasnin, a new human granulocyte elastase inhibitor produced by a strain of Streptomyces. Biochem. Biophys. Res. Commun., 83, 704-709 (1978).
145) Y. Iwai, A. Kora, Y. Takahashi, T. Hayashi, J. Awaya, R. Masuma, R. Oiwa, and S. Ōmura: Production of deoxyfrenolicin and a new antibiotic, frenolicin by Streptomyces roseofulvus strain AM-3867. J. Antibiot., 31, 959-965 (1978).
146) S. Ōmura, H. Tanaka, Y. Iwai, K. Nishigaki, J. Awaya, Y. Takahashi, and R. Masuma: A new antibiotic, setomimycin, produced by a strain of Streptomyces. J. Antibiot., 31, 1091-1098 (1978).
147) H. Ohno, T. Saheki, J. Awaya, A. Nakagawa, and S. Ōmura: Isolation and characterization of elasnin, a new human granulocyte elastase inhibitor produced by a strain of Streptomyces. J. Antibiot., 31, 1116-1123 (1978).
148) A Furusaki, N. Hashiba, T. Matsumoto, A. Hirano, Y. Iwai, and S. Ōmura: X-ray crystal structure of staurosporine: a new alkaloid from Streptomyces strain. J. Chem. Soc. Chem. Commun., 1978, 800-801 (1978).
149) S. Ōmura, C, Kitao, H. Hamada, and H. Ikeda: Bioconversion and biosynthesis of 16-membered macrolide antibiotics. X. Final steps in the biosynthesis of spiramycin, using enzyme inhibitor: cerulenin. Chem. Pharm. Bull., 27, 176-182 (1979).
150) S. Ōmura and J. Awaya: Lipid metabolism and antibiotic cerulenin, inhibitor of fatty acid synthesis. (Review article). Yakugaku, 28, 75-80 (1979).
151) H. Tanaka, R. Oiwa, S. Matsukura, and S. Ōmura: Amphomycin inhibits phospho-N-acetylmuramyl-pentapeptide translocase in peptidoglycan synthesis of Bacillus. Biochem. Biophys. Res. Commun., 86, 902-908 (1979).
152) S. Ōmura and Y. Iwai: Microbial alkaloid (Review article). Hakko to Kogyo, 37, 223-234 (1979).
153) S. Ōmura, Y. Iwai, Y. Takahashi, N. Sadakane, A. Nakagawa, H. Oiwa, Y. Hasegawa, and T. Ikai: Herbimycin, a new antibiotic produced by a strain of Streptomyces. J. Antibiot., 32, 255-261 (1979).
154) S. Okubo, N. Nakamura, K. Ito, H. Marumo, M. Tanaka, and S. Ōmura: Antitumor activity of prumycin. J. Antibiot., 32, 347-354 (1979).
155) R. W. Burg, B. M. Miller, E. E. Baker, J. Birnbaum, S. A. Currie, R. Hartman, Y. -L. Kong, R. Monaghan, G. Olson, I. Putter, J. B. Tunac, H. Wallick, E. O. Stapley, R. Oiwa, and S. Ōmura: Avermectins, new family of potent anthelmintic agents: producing organism and fermentation. Antimicrob. Agents Chemother., 15, 361-367 (1979).
156) C. Kitao, J. Miyazawa, and S. Ōmura: Induction of the bioconversion of leucomycins by glucose and its regulation by butyrate. Agricult. Biol.Chem., 43, 833-839 (1979).
157) M. Kasai, K. Shirahata, S. Ishi, K. Mineura, H. Marumo, H. Tanaka, and S. Ōmura: Structure of nanaomycin E, a new nanaomycin. J. Antibiot., 32, 442-445 (1979).
158) C. Kitao, H. Ikeda, H. Hamada, and S. Ōmura: Bioconversion and biosynthesis of 16-membered macrolide antibiotics. XIII. Regulation of spiramycin I 3-hydroxyl acylase formation by glucose, butyrate, and cerulenin. J. Antibiot., 32, 593-599 (1979).
159) H. Tanaka, S. Shimizu, R. Oiwa, Y. Iwai, and S. Ōmura: The site of inhibition of cell wall synthesis by 3-amino-3-deoxy-D-glucose in Staphylococcus aureus. J. Biochem., 86, 155-159 (1979).
160) K. Kakinuma, N. Ikekawa, A. Nakagawa, and S. Ōmura: The structure of asukamycin, a possible shunt metabolite from 3-dehydroquinic acid in the shikimate pathway. J. Am. Chem. Soc., 101, 3402-3404 (1979).
161) S. Ōmura, A. Nakagawa, and H. Ohno: Structure of elasnin, a novel elastase inhibitor. J. Am. Chem. Soc., 101, 4386-4388 (1979).
162) S. Ōmura and C. Kitao: Biosynthesis of macrolide antibiotics (Review article). Hakko to Kogyo, 37, 749-764 (1979).
163) A. Hirano, Y. Iwai, R. Masuma, K. Tei, and S. Ōmura: Neoxaline, a new alkaloid produced by Aspergillus japonicus. Production, isolation and properties. J. Antibiot., 32, 781-785 (1979).
164) S. Ōmura, A. Hirano, Y. Iwai, and R. Masuma: Herquline, a new alkaloid produced by Penicillium herquei. Fermentation, isolation and properties. J. Antibiot., 32, 786-790 (1979).
165) P. Bartner, D. L. Boxler, R. Brambilla, A. K. Mallams, J. B. Morton, P. Reichert, F. D. Sancilio, H. Surprenant, G. Tomalesky, G. Lukacs, A. Olesker, T. T. Thang, L. Valente, and S. Ōmura: The megalomicins. Part 7. A structural revision by carbon-13 nuclear magnetic resonance and X-ray crystallography. Synthesis and conformational analysis of 3-dimethylamino- and 3-azido-D- and -L-hexopyranosides, and the crystal structure of 4"-O-(4-iodobenzoyl)megalomicin A. J. Chem. Soc. Perkin I, 1979, 1600-1624 (1979).
166) S. Ōmura, A. Nakagawa, and N. Sadakane: Structure of herbimycin, a new ansamycin antibiotic. Tetrahedron Lett., 1979, 4323-4326 (1979).
167) S. Ōmura, H. Tanaka, R. Oiwa, T. Nagai, Y. Koyama, and Y. Takahashi: Studies on bacterial cell wall inhibitors. VI. Screening method for the specific inhibitors of peptidoglycan synthesis. J. Antibiot., 32, 978-984 (1979).
168) S. Ōmura, H. Tanaka, Y. Tanaka, P. Spiri-Nakagawa, R. Oiwa, Y. Takahashi, K. Matsuyama, and Y. Iwai: Studies on bacterial cell wall inhibitors. VII. Azureomycins A and B, new antibiotics produced by Pseudonocardia azurea nov. sp. Taxonomy of the producing organism, isolation, characterization and biological properties. J. Antibiot., 32, 985-994 (1979).
169) P. Spiri-Nakagawa, Y. Tanaka, R. Oiwa, H. Tanaka, and S. Ōmura: Studies on bacterial cell wall inhibitors. VIII. Mode of action of a new antibiotic, azureomycin B in Bacillus cereus T. J. Antibiot., 32, 995-1001 (1979).
170) J. Awaya, K. Matsuyama, Y. Iwai, and S. Ōmura: Production of 9-b-D-arabinofuranosyl-adenine by a new species of Streptomyces and its herbicidal activity. J. Antibiot., 32, 1050-1054 (1979).
171) C. Kitao, H. Hamada, H. Ikeda, and S. Ōmura: Bioconversion and biosynthesis of 16-membered macrolide antibiotics. XV. Final steps in the biosynthesis of leucomycins. J. Antibiot., 32, 1055-1057 (1979).
172) S. Ōmura, H. Ikeda, and C. Kitao: The detection of a plasmid in Streptomyces ambofaciens. KA-1028 and its possible involvement in spiramycin production. J. Antibiot., 32, 1058-1060 (1979).
173) A. Kawaguchi, H. Tomoda, S. Okuda, J. Awaya, and S. Ōmura: Cerulenin resistance in a cerulenin-producing fungus. Isolation of cerulenin insensitive fatty acid synthetase. Arch. Biochem. Biophys., 197, 30-35 (1979).
174) S. Ōmura, H. Ikeda, and C. Kitao: Isolation and properties of spiramycin I 3-hydroxyl acylase from Streptomyces ambofaciens. J. Biochem., 86, 1753-1758 (1979).
175) S. Ōmura and H. Sakakibara: Chemical modification of 16-membered macrolide antibiotics (Review article). Hakko to Kogyo 37, 1171-1186 (1979).
176) Y. Iwai, A. Nakagawa, A. Nagai, K. Matsuyama, Y. Takahashi, M. Yamashita, A. Hirano, and S. Ōmura: 2'-Amino-2'-deoxyadenosine produced by a strain of Actinomadura. J. Antibiot., 32, 1367-1369 (1979).