Synthesis and antibacterial activity of derivatives of the glycopeptide antibiotic A-40926 and its aglycone

Journal of Antibiotics

Volumn 49, Issue 12, 1996, Pages 1236-1248

  Hermann, Rolf ^b   Ripamonti, Franca ^a   Romanò, Gabriella ^a   Restelli, Ermenegildo ^a   Ferrari, Pietro ^a   Goldstein, Beth P ^c   Berti, Marisa ^a   Ciabatti, Romeo ^a  

^a Gruppo Lepetit SpA   (Italy)

^b Applied Microbiology Inc ^*  (Germany)

^c Applied Microbiology Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC A40926; ANTIBIOTIC AGENT; DRUG DERIVATIVE; ESTER DERIVATIVE; GLYCOPEPTIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NEISSERIA GONORRHOEAE; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SEPTICEMIA; STREPTOCOCCUS PYOGENES; STRUCTURE ACTIVITY RELATION;

EID: 0030449673     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.49.1236     Document Type: Article

References (23)

1. GOLDSTEIN, B. P.; E. SELVA, L. GASTALDO, M. BERTI, R. PALLANZA, F. RIPAMONTI, P. FERRARI, M. DENARO, V. ARIOLI & G. CASSANI: A-40926, a new glycopeptide antibiotic with anti-Neisseria activity. Antimicrob. Agents Chemother. 31: 1961-1966, 1987
2. CORTI, A. & G. CASSANI: Synthesis and characterisation of D-alanyl-D-alanine agarose: A new bioselective adsorbent for affinity chromatography of glycopeptide antibiotics. Appl. Biochem. Biotechnol. 11: 101-109, 1985
3. BARNA, J. C. J. & D. H. WILLIAMS: The structure and mode of action of glycopeptide antibiotics of the vancomycin group. Ann. Rev. Microbiol. 38: 339-357, 1984
4. CHRISTENSEN, S. B.; H. S. ALLAUDEEN, M. R. BURKE, S. A. CARR, S. K. CHUNG, P. DE PHILLIPS, J. J. DINGERDISSEN, M. DI PAOLO, A. J. GIOVENELLA, S. L. HEAD, L. B. KILLMER, B. A. MICO, L. MUELLER, C. H. PAN, B. L. POEHLAND, J. B. RAKE, M. C. SHEARER, R. D. SITRIN, L. J. NISBET & P. W. JEFFS: Parvodicin, a novel glycopeptide from a new species, Actinomadura parvosata: Discovery, taxonomy, activity and structure elucidation. J. Antibiotics 40: 970-990, 1987
5. WATANAKUNAKORN, C.: The antibacterial action of vancomycin. Rev. Infectious Diseases, Vol. 3, Suppl., 1981
6. PALLANZA, R.; M. BERTI, B. P. GOLDSTEIN, E. MAPELLI, E. RANDISI, R. SCOTTI & V. ARIOLI: Teichomycin, in vitro and in vivo evaluation in comparison with other antibiotics. J. Antimicrob. Chemother. 11: 419-424, 1983
7. SHEARER, M. C.; P. ACTOR, B. A. BOWIE, S. F. GRAPPEL, C. H. NASH, D. J. NEWMAN, Y. K. OH, C. H. PAN & L. J. NISBET: Aridicins, novel glycopeptide antibiotics. I. Taxonomy, production and biological activity. J. Antibiotics 38: 555-560, 1985
8. SHEARER, M. C.; A. J. GIOVENELLA, S. F. GRAPPEL, R. D. HEDDE, R. J. MEHTA, Y. K. OH, C. H. PAN, D. H. PITKIN & L. J. NISBET: Kibdelins, novel glycopeptide antibiotics. I. Discovery, production and biological evaluation. J. Antibiotics 39: 1386-1394, 1986
9. TAKATSU, T.; T. KATAYAMA, M. NAKAJIMA, S. TAKAHASHI, T. HANEISHI, T. MAGARIBUCHI & M. TAJIMA: Chloropolysporins A, B and C, novel glycopeptide antibiotics from Faenia interiecta sp. nov. V. Comparative studies of the biological properties. J. Antibiotics 40: 946-952, 1987
10. WALTHO, J. P.; D. H. WILLIAMS, E. SELVA & P. FERRARI: Structure elucidation of the glycopeptide antibiotic complex A-40926. J. Chem. Soc. Perkin Trans. I 1987: 2103-2107, 1987
11. SELVA, E.; B. P. GOLDSTEIN, P. FERRARI, R. PALLANZA, E. RIVA, M. BERTI, A. BORGHI, G. BERETTA, R. SCOTTI, G. ROMANÒ, G. CASSANI, V. ARIOLI & M. DENARO: A-40926 aglycone and pseudoaglycones: Preparation and biological activity. J. Antibiotics 41: 1243-1252, 1988
12. MALABARBA, A.; A. TRANI, P. FERRARI, R. PALLANZA & B. CAVALLERI: Synthesis and biological activity of some esters of the N-acetylglucosaminyl aglycone and of the aglycone of teicoplanin. J. Antibiotics 40: 1572-1587, 1987
13. BOECK, LA VERNE D. & F. D. MERTZ: A-47934, a novel glycopeptideaglycone antibiotic produced by a strain of Streptomyces toyocaensis. Taxonomy and fermentation studies. J. Antibiotics 39: 1533-1540, 1986
14. MALABARBA, A.; A. TRANI, P. STRAZZOLINI, G. CIETTO, P. FERRARI, G. TARZIA, R. PALLANZA & M. BERTI: Synthesis and biological properties of N 3- carboxamides of teicoplanin antibiotics. Structure-activity relationship. J. Med. Chem. 32: 2450-2460, 1989
15. CHUNG, S. K.; P. TAYLOR, Y. K. OH, C. DE BROSSE & P. W. JEFFS: Biosynthetic studies of aridicin antibiotics. I. Labelling patterns and overall pathways. J. Antibiotics 34: 642-651, 1986
16. HUBER, F. M.; K. H. MICHEL, A. H. HUNT, J. W. MARTIN & R. M. MOLLOY: Preparation and characterization of some bromine analogs of the glycopeptide antibiotic actaplanin. J. Antibiotics 41: 798-801, 1988
17. CAVALLERI, B.; P. FERRARI, A. MALABARBA, A. MAGNI, R. PALLANZA & G. G. GALLO: Teicoplanin, antibiotics from Actinoplanes teichomyceticus nov. sp. VIII. Opening of the polypeptide chain of teicoplanin aglycone under hydrolytic conditions. J. Antibiotics 40: 49-59, 1987
18. FINNEY, D. J.: The Spearman-Kaerber method. In: Statistical Method in Biological Assay, pp. 524-530, Charles Griffin & Co., Ltd., London, 1952
19. WILLIAMSON, M. P.; D. H. WILLIAMS & S. J. HAMMOND: Interactions of vancomycin and ristocetin with peptides as a model for protein binding. Tetrahedron 40: 569-577, 1984
20. BARNA, J. C. J.; D. H. WILLIAMS & M. P. WILLIAMSON: Structural features that affect the binding of teicoplanin, ristocetin A, and their derivatives to the bacterial cell-wall model N-acetyl-D-alanyl-D-alanine. J. Chem. Soc., Chem. Comm. 254-256, 1985
21. HERRIN, T. R.; A. M. THOMAS, T. J. PERUN, J. C. MAO & S. W. FESIK: Preparation of biologically active ristocetin derivatives: Replacement of the 1′-amino group. J. Med. Chem. 28: 1371-1375, 1985
22. 63-carboxypeptides of teicoplanin and teicoplanin aglycone. J. Antibiotics 42: 1800-1816, 1989
23. IRANI, A.; P. FERRARI, R. PALLANZA & G. TARZIA: Deaminoteicoplanin and its derivatives. Synthesis, antibacterial activity and binding strength to Ac-D-Ala-D-Ala. J. Med. Chem. 32: 310-314, 1989