Pyranmycin

Designs involving disaccharide have also been attempted (Fignre 4.5). However, disaccharide-based aminoglycosides are less active in general. For example, the designs of 45 and 46 that mimic rings 11 and 111 of pyranmycin were found to be inactive. 

Pyranmycin which contains both D-pyranose and L-pyranose at ring III, has been synthesized (Scheme 4.16). The p-glycosidic bond between rings II and... 

Scheme 4.19. Synthesis of 3, 4 -dideoxy kanamycin B analog and pyranmycin.

Scheme 4.22. Synthesis of pyranmycin and kanamycin B analogs with AHB group at N-1.

Elchert B, Li J, Wang J, Hui Y, Rai R, Ptak R, Ward P, Takemoto JY, Ben-saci M, Chang C-WT. Application of the synthetic amino sugars for glyco-diversification synthesis and antimicrobial studies of pyranmycin. J Org Chem 2004 69 1513-1523. 

Pyranmycin which contains various D-pyranoses and L-pyranoses on ring III have been synthesized (Scheme 1). (73,14) The 3-glycosidic bond between... 

Figure 2. Structural Relationship between Neomycin and Pyranmycin...

Table I. Minimum Inhibitory Concentration and Binding Scores of the Synthesized Pyranmycins ...

Copyright (2005) from (Novel Method for the Synthesis of 3, 4-Dideoxygenated Pyranmycin and Kanamycin Compounds, and Studies of Their Antibacterial Activity against Aminoglycoside Resistant Bacteria) by (Cheng-Wei Tom Chang). Reproduced by permission of Taylor Francis Group. LLC., http//www.taylorandfrancis.com. 

The constructed N-1 modified pyranmycin was assayed against aminoglycoside susceptible and resistant strains of Escherichia coli using ribostamycin, and butirosin as the controls. From the MIC values, the synthesized aminoglycoside with the attachment of AHB group at N-1 regain the activity against both resistant strains of bacteria (Table III). 

The corresponding pyranmycin without AHB group at N-1 plasmid encoded for AAC6VAPH2"... 

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