Reductive alkylation of glycopeptide antibiotics: Synthesis and antibacterial activity

Journal of Antibiotics

Volumn 49, Issue 6, 1996, Pages 575-581

  Cooper, Robin D G ^a   Snyder, Nancy J ^a   Zweifel, Mark J ^a   Staszak, Michael A ^a   Wilkie, Stephen C ^a   Nicas, Thalia I ^a   Müllen, Deborah L ^a   Butler, Thomas F ^a   Rodriguez, Michael J ^a   Huff, Bret E ^a   Thompson, Richard C ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; CHLOROORIENTICIN A; DRUG DERIVATIVE; GLYCOPEPTIDE; LY 307599; ORITAVANCIN; UNCLASSIFIED DRUG; VANCOMYCIN;

ALKYLATION; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENTEROCOCCUS; NONHUMAN; PRIORITY JOURNAL;

EID: 8944258105     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.49.575     Document Type: Article

References (15)

1. LECLERCQ, R.; E. DERLOT, J. DUVAL & P. COURVALIN: Plasmid-mediated resistance to vancomycin and teicoplanin in Enterococcus faecium. New Eng. J. Med. 319: 157-161, 1988
2. UTTLEY, A. H. C.; C. H. COLLINS, J. NAIDOO & R. C. GEORGE: Vancomycin-resistant enterococci, Lancet i: 57-58, 1988
3. NAGARAJAN, R.; A. A. SCHABEL, J. L. OCCOLOWITZ, F. T. COUNTER, J. L. OTT & A. M. FELTY-DUCKWORTH: Synthesis and antibacterial activity of N-alkyl vancomycins. J. Antibiotics 42: 63-72, 1989
4. NAGARAJAN, R. : Structure-activity relationships of vancomycin-type glycopeptide antibiotics. J. Antibiotics 46: 1181-1195, 1993
5. NICAS, T. I.; D. L. MÜLLEN, J. E. FLOKOWITSCH, D. A. PRESTON, N. J. SNYDER, R. E. STRATFORD & R. D. G. COOPER: Activities of the semisynthetic glycopeptide LY191145 against vancomycin-resistant enterococci and other gram-positive bacteria. Antimicrob. Agents Chemother. 39: 2585-2587, 1995
6. PAVLOV, A. Y.; E. N. OLSUFYEVA, T. F. BERDNIKOVA, I. V. MALKOVA, M. N. PRKEBRAZHENSKAYA & G. D. RISBRIDGER: Modification of glycopeptide antibiotic eremomycin by the action of alkyl halides and study on antibacterial activity of the compounds obtained. J. Antibiotics 47: 225-232, 1994
7. LOMAKINA, N. N.; T. F. BERDNIKOVA, N. L. TOKAREVA, E. A. ABRAMOVA & N. Y. DOKSHINA: Structure of eremomycin, a novel polycyclic glycopeptide antibiotic. Antibiot. Khimioter. 34: 254-258, 1989
8. NAGARAJAN, R.; D. M. BERRY, A. H. HUNT, J. L. OCCOLOWITZ & A. A. SCHABEL: Conversion of antibiotic A82846B to orienticin A and structural relationships of related antibiotics. J. Org. Chem. 54: 983-986, 1989
9. TSUJI, N.; T. KAMIGAUCHI, M. KOBAYASHI & Y. TERUI: New glycopeptide antibiotics: II. The isolation and structures of chloroorienticins. J. Antibiotics 41: 1506-1510, 1988
10. NAGARAJAN, R.; D. M. BERRY & A. A. SCHABEL: The structural relationships of A82846B and its hydrolysis products with chloroorienticins A, B and C. J. Antibiotics 42: 1438-1440, 1989
11. NAGARAJAN, R.; A. A. SCHABEL, J. L. OCCOLOWITZ, F. T. COUNTER & J. L. OTT: Synthesis and antibacterial activity of N-acyl vancomycins. J. Antibiotics 41: 1430-1438, 1988
12. ROBERTS, G. D.; S. A. CARR, S. ROTTSCHAEFER & P. W. JEFFS: Structural characterization of glycopeptide antibiotics related to vancomycin by fast atom bombardment mass spectrometry. J. Antibiotics 38: 713-720, 1985
13. LINK, P. A. J.; H. C. VAN DER PLAS & F. MULLER: Synthesis of water soluble 8-substituted 5-deazaflavins. J. Heterocyclic Chem. 22: 873-878, 1985
14. HARRIS, C. M.; R. KANNAN, H. KOPECKA & T. M. HARRIS: The role of the chlorine substituents in the antibiotic vancomycin: preparation and characterization of monoand didechlorovancomycin. J. Am. Chem. Soc. 107: 6652-6658, 1985
15. GERHARD, U.; J. P. MACKAY, R. A. MAPLESTONE & D. H. WILLIAMS: The role of the sugar and chlorine substituents in the dimerization of vancomycin antibiotics. J. Am. Chem. Soc. 115: 232-237, 1993