Selective inhibition of the bacterial peptidoglycan biosynthesis by the new types of liposidomycins

Journal of Antibiotics

Volumn 51, Issue 12, 1998, Pages 1099-1104

  Kimura, Ken Ichi ^a   Ikeda, Yoshikazu ^a   Kagami, Shinobu ^a   Yoshihama, Makoto ^a   Suzuki, Katsuhiro ^b   Osada, Hiroyuki ^c   Isono, Kiyoshi ^c  

^a SNOW BRAND MILK PRODUCTS CO LTD   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYLGLUTARIC ACID; ANTIINFECTIVE AGENT; GLYCOPROTEIN; LIPOSIDOMYCIN DERIVATIVE; PEPTIDOGLYCAN; SULFATE; TUNICAMYCIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CELL STRAIN 3T3; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SELECTIVITY; DRUG STRUCTURE; GLYCOPROTEIN SYNTHESIS; MOUSE; MYCOBACTERIUM PHLEI; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 0032428375     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.51.1099     Document Type: Article

References (19)

1. BUGG, T. D. H. & C. T. WALSH: Intracellular steps of bacterial cell wall peptidoglycan biosynthesis: Enzymology, antibiotics, and antibiotic resistance. Nat. Prod. Rep. 9: 199-215, 1992
2. BUGG, T. D. H. & P. E. BRANDISH: From peptidoglycan to glycoproteins: Common features of lipid-linked oligosaccharide biosynthesis. FEMS Microbiology Letters 119: 255-262, 1994
3. UBUKATA, M.; K. ISONO, K. KIMURA, C. C. NELSON & J. A. MCCLOSKEY: The structure of liposidomycin B, an inhibitor of bacterial peptidoglycan synthesis. J. Am. Chem. Soc. 110: 4416-4417, 1988
4. UBUKATA, M.; K. KIMURA, K. ISONO, C. C. NELSON, J. M. GREGSON & J. A. MCCLOSKEY: Structure elucidation of liposidomycins, a class of complex lipid nuclcoside antibiotics. J. Org. Chem. 57: 6392-6403, 1992
5. ISONO, K.; M. URAMOTO, H. KUSAKABE, K. KIMURA, K. IZAKI, C. C. NELSON & J. A. MCCLOSKEY: Liposidomycins: novel nucleoside antibiotics which inhibit bacterial peptidoglycan synthesis. J. Antibiotics 38: 1617-1621, 1985
6. KIMURA, K.; N. MIYATA, G. KAWANISHI, Y. KAMIO, K. IZAKI & K. ISONO: Liposidomycin C inhibits phospho-N-acetylmuramyl-pentapeptide transferase in peptidoglycan synthesis. Agric. Biol. Chem. 53: 1811-1815, 1989
7. TAMURA, G.; T. SASAKI, M. MATSUHASHI, A. TAKATSUKI & M. YAMASAKI: Tunicamycin inhibits the formation of lipid intermediate in cell-free peptidoglycan synthesis of bacteria. Agric. Biol. Chem. 40: 447-449, 1976
8. INUKAI, M.; F. ISONO & A. TAKATSUKI: Selective inhibition of the bacterial translocase reaction in peptidoglycan synthesis by mureidomycins. Antimicrob. Agents Chemother. 37: 980-983, 1993
9. BRANDISH, P. E.; K. KIMURA, M. INUKAI, R. SOUTHGATE, J. T. LONSDALE & T. D. H. BUGG: Modes of action of tunicamycin, liposidomycin B, and mureidomycin A: inhibition of phospho-N-acetylmuramyl-pentapeptide translocase from Escherichia coli. Antimicrob. Agents Chemother. 40: 1640-1644, 1996
10. MUROI, M.; K. KIMURA, H. OSADA, M. INUKAI & A. TAKATSUKI: Liposidomycin B inhibits in vitro formation of polyprenyl(pyro)phosphate N-acetylglucosamine, an intermediate in glycoconjugate biosynthesis. J. Antibiotics 50: 103-104, 1997
11. KIMURA, K.; S. KAGAMI, Y. IKEDA, H. TAKAHASHI, M. YOSHIHAMA, H. KUSAKABE, H. OSADA & K. ISONO: New types of liposidomycins that inhibit bacterial peptidoglycan synthesis and are produced by Streptomyces. I. Producing organism and medium components. J. Antibiotics 51: 640-646, 1998
12. KIMURA, K.; Y. IKEDA, S. KAGAMI, M. YOSHIHAMA, M. UBUKATA, Y. ESUMI, H. OSADA & K. ISONO: New types of liposidomycins that inhibit bacterial peptidoglycan synthesis and are produced by Streptomyces. II. Isolation and structure elucidation. J. Antibiotics 51: 647-654, 1998
13. PARODI, A. J.; N. H. BEHRENS, L. F. LELOIR & H. CARMINATTI: The role of polyprenyl-bound saccharides as intermediates in glycoprotein synthesis in liver. Proc. Natl. Acad. Sci. USA. 69: 3268-3272, 1972
14. MOSMANN, T.: Rapid colorimetric assay for cellular growth and survival : Application to proliferation and cytotoxicity assays. J. Immunol. Methods. 65: 55-63, 1983
15. TANAKA, H.; R. OIWA, S. MATSUKURA & S. OMURA: Amphomycin inhibits phospho-N-acetylmuramyl-pentapeptide translocase in peptidoglycan synthesis of Bacillus. Biochem. Biophys. Res. Commun. 86: 902-908, 1979
16. TAKATSUKI, A.; K. KAWAMURA, M. OKINA, Y. KODAMA, T. ITO & G. TAMURA: The structure of tunicamycin. Agric. Biol. Chem. 41: 2307-2309, 1977
17. TAMURA, G.; T. SASAKI, M. MATSUHASHI, A. TAKATSUKI & M. YAMASAKI: Tunicamycin inhibits the formation of lipid intermediates in cell-free peptidoglycan synthesis of bacteria. Agric. Biol. Chem. 40: 447-449, 1976
18. TAMURA, G. & A. TAKATSUKI: Selective inhibition of the formation of polyisoprenol (pyro) phosphate N-acetylglucosamine by tunicamycin. Proc. Japan Acad. 56 (Ser. B): 251-256, 1980
19. HEIFETZ, A.; R. W. KEENAN & A. D. ELBEIN: Mechanism of action of tunicamycin on the UDP-GlcNAc: dolichylphosphate GlcNAc-1-phosphate transferase. Biochemistry 18: 2186-2192, 1979