Tuning the Regioselectivity of the Staudinger Reaction for the Facile Synthesis of Kanamycin and Neomycin Class Antibiotics with N-1 Modification

Tuning the Regioselectivity of the Staudinger Reaction for the Facile Synthesis of Kanamycin and Neomycin Class Antibiotics with N-1 Modification

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-...

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Veröffentlicht in:Organic letters 2005-07, Vol.7 (14), p.3061-3064
Hauptverfasser: Li, Jie, Chen, Hsiao-Nung, Chang, Huiwen, Wang, Jinhua, Chang, Cheng-Wei Tom
Format: Artikel
Sprache:eng
Schlagworte:
Amikacin - pharmacology
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - classification
Drug Resistance, Microbial
Escherichia coli - drug effects
Kanamycin - analogs & derivatives
Kanamycin - chemical synthesis
Kanamycin - chemistry
Microbial Sensitivity Tests
Molecular Structure
Neomycin - chemical synthesis
Neomycin - chemistry
Stereoisomerism
Structure-Activity Relationship
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Zusammenfassung: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‘ ‘).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol051045d