Tuning the regioselectivity of the Staudinger reaction for the facile synthesis of kanamycin and neomycin class antibiotics with N-1 modification.
[reaction: see text] A novel method for achieving the desired regioselective reduction of the N-1 azido group on a tetraazidoneamine has been developed that leads to the synthesis of both kanamycin and neomycin class antibiotics bearing N-1 modification. Both classes of aminoglycosides are active against aminoglycoside-resistant bacteria carrying APH(3')-I and AAC(6')/APH(2'').
Department of Chemistry and Biochemistry, Utah State University, Logan, 84322-0300, USA.
Jie
J
Li
Hsiao-Nung
HN
Chen
Huiwen
H
Chang
Jinhua
J
Wang
Cheng-Wei Tom
CW
Chang
D000583:Amikacin / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000145:classification; D004352:Drug Resistance, Microbial; D004926:Escherichia coli / Q000187:drug effects*; D007612:Kanamycin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009355:Neomycin / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; C509796:JLN027; D007612:Kanamycin; D000583:Amikacin; D009355:Neomycin