Biological transformation of kanamycin A to amikacin (BBK-8)

Investigation of the Regioselectivity for the Staudinger Reaction and Its Application for the Synthesis of Aminoglycosides with N-1 Modification

“…Splitting patterns were designed as s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet. 13 C NMR spectra were obtained by broad-band WALTZ decoupling using 100 MHz spectrometer. All NMR spectra were recorded at ambient temperature unless otherwise noted.…”

“…In general, these methods utilize metal-mediated chelation, 5-9 cyclization between the selected carbamate-protected amino group and its vicinal hydroxyl group 10-12 or enzymatic approaches. 13 However, selectivity of these strategies closely depends on the scaffolds of parent aminoglycosides. In addition, there is no applicable method for regioselective differentiation of the azido groups on perazidoaminoglycosides.…”

Astonishing diversity of natural surfactants: 4. Fatty acid amide glycosides, their analogs and derivatives

“…Amikacin 1 inhibits the growth of resistant bacteria producing APH(3′)-1 (3′-aminoglycoside phosphotransferase) and AAD(2′) (2′amino acid decarboxylase). Amikacin 1 was biologically transformed from kanamycin by a mutant of butirosin-producing Bacillus circulans (26). Arbekacin 2 showed strong activity against resistant bacteria including Pseudomonas.…”

Aminoglycosides and Aminocyclitols (Other Than Streptomycin)

“…In addition, hybrimycin-type antibiotics were coproduced with neomycin, kanamycin and LL-BM408 (Borders et al 1982). Amikacin (Cappelletti and Spagnoli 1983) and 1-epidactimicin (Morioka et al 1989) were obtained by microbial conversion of kanamycin and fortimicin B, respectively; for the first a mutant of a butirosin-producing strain of Bacillus circulans was used, and for the second a mutated istamycin-producing strain of Streptomyces tenjimariensis.…”