Cladinose analogues of sixteen-membered macrolide antibiotics: I. Synthesis of 4-O-Alkyl-L-cladinose analogues via glycosylation

Journal of Antibiotics

Volumn 49, Issue 6, 1996, Pages 582-592

  Kurihara, Ken Ichi ^a   Ajito, Keiichi ^a   Shibahara, Seiji ^a   Ishizuka, Tsuneo ^a   Hara, Osamu ^a   Araake, Minako ^a   Omoto, Shoji ^a  

^a MEIJI SEIKA KAISHA LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOMYCIN; DRUG ANALOG; MACROLIDE; MIDECAMYCIN;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; PLASMA; PRIORITY JOURNAL; RAT;

EID: 0030018608     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.49.582     Document Type: Article

References (19)

1. OMURA, S. (Ed.): Macrolidc Antibiotics. Chemistry, Biology, and Practice. Academic Press Inc., 1984
2. OKAMOTO, R.; T. FUKUMOTO, K. IMAFUKU, T. OKUBO, K. KIYOSHIMA, A. TAKAMATSU & T. TAKEUCHI: Screening for 16-membered macrolide-transforming microorganisms. J. Ferment. Technol. 57: 519-528, 1979
3. SHOMURA, T.; S. SOMEYA, K. UMEMURA, M. NISHIO & S. MURATA: Metabolism of 9,3"-diacetylmidecamycin. I. The metabolic fate of 9,3"-diacetylmidecamycin. Yakugaku Zasshi (Japanese) 102: 781-795, 1982
4. SANO, H.; T. SUNAZUKA, H. TANAKA, K. YAMASHITA, R. OKACHI & S. OMURA: Chemical modification of spiramycins. III. Synthesis and antibacterial activities of 4"-sulfonates and 4"-alkylethers of spiramycin I. J. Antibiotics 37: 750-759, 1984
5. TATSUTA, K.; A. TANAKA, M. KINOSHITA & S. UMEZAWA: Synthesis of cladinose analogues of carbomycin B. Chem. Lett. 1977: 769-772, 1977
6. MAJER, J.; J. R. MARTIN, R. S. EGAN & J. W. CORCORAN: Antibiotic glycosides. 8. Erythromycin D, a new macrolide antibiotic. J. Am. Chem. Soc. 99: 1620-1622, 1977
7. OMOTO, S.; K. IWAMATSU, S. INOUYE & T. NIIDA: Modifications of a macrolide antibiotic midecamycin (SF-837). I. Synthesis and structure of 9,3"-diacetylmidecamycin. J. Antibiotics 29: 536-548, 1976
8. YOSHIDA, T.; T. WATANABE, T. SHOMURA, S. SOMEYA, R. OKAMOTO, S. ISHIHARA, K. MIYAUCHI & Y. KAZUNO: Bacteriological evaluation of midecamycin acetate and its metabolites. Jpn. J. Antibiotics 35: 1462-1474, 1982
9. 5 (TMS-19-Q). J. Antibiotics 34: 1001-1010, 1981
10. SAKAKIBARA, H.; O. OKEKAWA, T. FUJIWARA, M. AIZAWA & S. OMURAI Acyl derivatives of l6-membered macrolides. II. Antibacterial activities and serum levels of 3"-O-acyl derivatives of leucomycin. J. Antibiotics 34: 1011-1018, 1981
11. WOODWARD, R. B.; E. LOGUSCH, K. P. NAMBIAR, K. SAKAN, D. E. WARD, B.-W. AU-PEUNG, P. BALARAM, L. J. BROWNE, P. J. CARD, C. H. CHEN, R. B. CHÊNEVERT, A. FLIRI, K. FROBEL, H.-J. GAIS, D. G. GARRATT, K. HAYAKAWA, W. HEGGIE, D. P. HESSON, D. HOPPE, I. HOPPE, J. A. HYATT, D. IKEDA, P. A. JACOBI, K. S. KIM, Y. KOBUKE, K. KOJIMA, K. KROWICKI, V. J. LEE, T. LEUTERT, S. MALCHENKO, J. MARTENS, R. S. MATTHEWS, B. S. ONG, J. B. PRESS, T. V. RAJAN BABU, G. ROUSSEAU, H. M. SAUTER, M. SUZUKI. K. TATSUTA, L. M. TOLBERT, E. A. TRUESDALE, I. UCHIDA, Y. UEDA, T. UYEHARA, A. T. VASELLA, W. C. VLADUCHICK, P. A. WADE, R. M. WILLIAMS & H. N.-C. WONG: Asymmetric total synthesis of erythromycin. 3. Total synthesis of erythromycin. J. Am. Chem. Soc. 103: 3215-3217, 1981
12. MALLAMS, A. K. & R. R. ROSSMAN: Novel 3-O-α-L- cladinosyl sixteen-membered macrolide antibacterials. J. Chem. Soc. Perkin Trans. I 1989: 799-805, 1989
13. FURUMAI, T. & M. SUZUKI: Studies on the biosynthesis of basic 16-membered macrolide antibiotics, platenomycins. II. Production, isolation and structures of 3-O-propionyl-5-O-mycaminosyl platenolides I and II, 9-dehydro demycarosyl platenomycin and demycarosyl platenomycin. J. Antibiotics 28: 775-782, 1975
14. 4. J. Antibiotics 24: 526-536, 1971
15. TATSUTA, K.; K. FUJIMOTO, M. KINOSHITA & S. UMEZAWA: A novel synthesis of 2-deoxy-a-glycosides. Carbohydr. Res. 54: 85-104, 1977
16. SUZUKI, K. & T. MUKAIYAMA: A novel method for the synthesis of 2-deoxydisaccharide by stereoselective cyclization of the acyclic precursor. Chem. Lett. 1982: 683-686, 1982
17. TOSHIMA, K.; S. MUKAIYAMA, T. YOSHIDA, T. TAMAI & K. TATSUTA: Application of efficient glycosylation of 2,6-anhydro-2-thio sugar to the total synthesis of erythromycin A. Tetrahedron Lett. 32: 6155-6158, 1991
18. SUZUKI, M.; T. FURUMAI, K. TAKEDA & T. SETOGUCHI (Tanabe Seiyaku Co., Ltd.): Fermentative production of macrolide antibiotic analogs. Jpn. Kokai 10288 (73), Feb. 8, 1973
19. WATANABE, T.; T. ISHII, K. MIYAUCHI, Y. KAZUNO, S. OMOTO, K. IWAMATSU, S. INOUYE & T. NIIDA: Antibacterial activities of 9- or 4"-acyl derivatives of midecamycin (SF-837) and 4"-depropionylmidecamycin. Chemotherapy 25: 1624-1629, 1977