I'm hydrolyzing some disaccharides and trisaccharides under mild acidic conditions to separate the monosacharides constituents, I have been questioned "why acid and not alkaline hydrolysis?"...in all protocols i have read about disaccharides uses acid conditions, and just a couple of them uses alkaline hydrolysis for polysaccharides and lipids, but nobody gives an explanation about why one or other method is more appropiate depending on the compound to be hydrolized. I hope you can give me a hand. Thank you.
Hi Francesco, acid hydrolysis is more generally applicable - you dont have to worry of there are any reactive groups such as amines in the reaction mixture (i.e. Tris-Buffer or ) or as a part of the carbohydrate (i.e. amide groups in chitin). In my experience, alkaline hydrolysates of carbohydrates end up more often than not as brown sludge, whereas TFA or HCl hydrolysis are much less troublesome.
To elaborate on Prof. Voglmeir's answer, there are reactions known as the Lobry de Bruyn–Alberda–van Ekenstein transformations that are much more readily catalyzed by base than by acid. These lead to isomerizations of the sugars, and can also lead to further reactions with amines, etc.
Thanks for the background information on these types of reactions to Dr. Cote.
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