Aminoglycosides are relatively stable in basic conditions, but it is readily cleaved by acid. Draw a mechanism for acid-catalyzed hydrolysis of an aliphatic aminoglycoside.

Detailed mechanism for acid-catalyzed hydrolysis of an aliphatic aminoglycoside.

Alternative mechanism for acid-catalyzed hydrolysis of an aliphatic aminoglycoside.

Another representation of the acid-catalyzed hydrolysis mechanism for aminoglycosides.

Final mechanism illustration for acid-catalyzed hydrolysis of an aliphatic aminoglycoside.