A new class of branched aminoglycosides: Pseudo-pentasaccharide derivatives of neomycin B

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3575-3578

  Fridman, Micha ^a   Belakhov, Valery ^a   Yaron, Sima ^b   Baasov, Timor ^a  

^a Department of Chemistry   (Israel)

^b TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLYCOSIDE; AMINOGLYCOSIDE DERIVATIVE; ANTIINFECTIVE AGENT; DRUG DERIVATIVE; FRAMYCETIN; OLIGOSACCHARIDE; OLIGOSACCHARIDES, BRANCHED CHAIN;

ADDITION REACTION; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACILLUS SUBTILIS; BACTERIAL STRAIN; CARBOHYDRATE ANALYSIS; CHEMISTRY; CONFORMATION; DRUG EFFECT; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; MICROBIOLOGICAL EXAMINATION; PATHOGENICITY; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; BACILLUS SUBTILIS; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; FRAMYCETIN; GRAM-NEGATIVE BACTERIA; MICROBIAL SENSITIVITY TESTS; OLIGOSACCHARIDES, BRANCHED-CHAIN; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0142106443     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035213i     Document Type: Article

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27. 1,2 = 4.5 Hz).
28. Complete NMR assignments for the monosaccharides 6-9, along with the protected pseudo-pentasaccharides 15a - d, and selected data for the unprotected 2-5 are given in Supporting Information.
29. Resistant strains included E. coli XL1(pET9d), Pseudomonas aeuriginosa (ATCC 27853), and Salmonella virchow (SV49). E. coli XL1-(pET9d) is an antibiotic-sensitive laboratory strain of E. coli that harbors plasmid pET9d with the cloned orf2 gene, which codes for aminoglycoside kinase APH(3′). P. aeuriginosa is a Gram-negative pathogen. The aph(3′)-IIb gene, which codes for APH(3′), is a chromosomal gene that was found in many clinical isolates of P. aeruginosa, including the ATCC 27853 strain, and likely accounts at least partly for the resistance of Pseudomonas to aminoglycosides (Hachler, H.; Santanam, P.; Kayser, F. H. Antimicrob. Agen. Chemother. 1996, 40, 1254-1256). S. virchow (SV49) is a clinical multidrug-resistant strain obtained from poultry and found to be resistant to streptomycin, tetracycline, ampicillin, sulfa, kanamycin, and neomycin. The mechanism(s) of resistance of this strain is still not known.
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32. Studies on the complete structure - activity relationship of ring V of designer pseudo-pentasaccharides are currently under investigation. We also intend to examine these newly designed structures as substrates/inhibitors of aminoglycoside-modifying enzymes to validate the postulated reduced interaction.