title: Synthesis of 2''-amino-2''-deoxyarbekacin and its analogs having potent activity against methicillin-resistant Staphylococcus aureus.
abstract: Based on our studies on the enzymatic modifications of arbekacin by methicillin-resistant Staphylococcus aureus (MRSA), replacement of the 2''-hydroxyl group by an amino group in arbekacin was designed to synthesize derivatives that would be active against MRSA. 2''-Amino-2''-deoxyarbekacin and five analogs were synthesized starting from dibekacin. Among them, 2''-amino-2''-deoxyarbekacin and the 5-epiamino analog showed excellent antibacterial activities against not only MRSA but also Gram-negative bacteria including Pseudomonas, and lower toxicities than arbekacin.
authors.affiliation: Institute of Microbial Chemistry, Tokyo, Japan.
authors.forename: S
authors.initials: S
authors.lastname: Kondo
authors.forename: Y
authors.initials: Y
authors.lastname: Ikeda
authors.forename: D
authors.initials: D
authors.lastname: Ikeda
authors.forename: T
authors.initials: T
authors.lastname: Takeuchi
authors.forename: T
authors.initials: T
authors.lastname: Usui
authors.forename: M
authors.initials: M
authors.lastname: Ishii
authors.forename: T
authors.initials: T
authors.lastname: Kudo
authors.forename: S
authors.initials: S
authors.lastname: Gomi
authors.forename: S
authors.initials: S
authors.lastname: Shibahara
mesh_terms: D002240:Carbohydrate Sequence; D003982:Dibekacin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006090:Gram-Negative Bacteria / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D016106:Methicillin Resistance; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D013210:Staphylococcus / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: C089087:2''-amino-2''-deoxyarbekacin; D003982:Dibekacin