Biosynthesis and Mutasynthesis of Aminoglycoside Antibiotics

Enantioselective Synthesis of N-Cbz-Protected 6-Amino-6-deoxymannose, -talose, and -gulose

“…Analysis of the aminoglycosides reveals two common structural motifs, a 2-deoxystreptamine core and variously substituted aminosugars (Scheme ). Wong and Mobashery have demonstrated the importance of the 6-amino-6-deoxysugar for both ribosomal RNA binding and antibiotic activity. , Previous structure−activity studies of the aminoglycoside antibiotics have used semisynthesis techniques to remove hydroxyl groups from the existing aminoglycosides and strategically added functional groups of interest …”

Aminoglycoside Antibiotics

“…[148][149][150] In an early strategy (mutasynthesis) for preparing new aminocyclitols, mutants of producing organisms were created by blocking formation of endogenous 2-DOS; these strains were then fed analogs of 2-DOS to be incorporated into new structures. [148][149][150] In an early strategy (mutasynthesis) for preparing new aminocyclitols, mutants of producing organisms were created by blocking formation of endogenous 2-DOS; these strains were then fed analogs of 2-DOS to be incorporated into new structures.…”

Glycobiotechnology: Enzymes for the synthesis of nucleotide sugars

“…7) consisting of a 14membered lactone ring which is substituted by a 2,6 dideoxyhexose (L-cladinose) and a 3, 4, 6 trideoxyhexose (D-desosamine) with a basic dimethylamino group [-74]. Streptomycin is an example from another family of antibiotics, the aminoglycosides, which are built up by cyclitols and deoxysugars [75]. Streptomycin (4) represents a pseudotrisaccharide with streptidine as a cyclitol structure and the deoxysugars dihydrostreptose and N-methyl-L-glucosamine (Fig.…”