Comparative chemistry of some aminoglycoside antibiotics
In the field of antibiotics, the term 'aminoglycoside' is restricted in its use to those compounds in which the aglycone is a cyclitol or an aminocyclitol; the sugar moieties usually contain at least one amino-group. The three clinically important groups are exemplified by streptomycin (I), neomycin (II) and kanamycm A (III). This paper will be concerned largely with the kanamycin group and particularly with the gentamicin C components (IV). Some discus. sion of structure determination will be included as well as some approaches to the synthesis of new aminoglycosides. In its most general sense, the term 'aminoglycoside' refers to any carbohydrate containing an amino-function and linked via the C-i oxygen to a second moiety—the aglycone. In the field of antibiotics, however, the term is restricted in its use to those compounds in which the aglycone is a cyclitol or an aminocyclitol. The clinically important aminoglycosides fall into three 'families' exemplified by streptomycin (I), neomycin (II) and kanamycin A (III). In streptomycin the aglycone is streptamine; in the other two cases OH HO'\3 HOH2C1,, HO I o OH HO>< HN NHCNH2 CNH NH OHC I