Abstract
Trifluoroacetolysis is a reaction which is carried out in mixtures of trifluoroacetic acid (TFA) and trifluoroacetic anhydride (TFAA). Under trifluoroacetolysis conditions which transamidate 2-acetamido-2-deoxy functions in sugar units into 2-deoxy-2-trifluoroacetamido groups, most reducing sugars and glycosides are stable due to the stabilizing effects of O-trifluoroacetyl groups formed by the action of TFA/TFAA on the hydroxyl groups of the sugar residues. Peptide bonds are cleaved by transamidation and thus proteins are degraded during trifluoroacetolysis. The trifluoroacetolysis reaction can be used for a number of specific degradations useful in studies of glycoconjugates:1Degradation of the protein part of glycoproteins with release of O- and N-glycosidically linked carbohydrate chains.2Specific degradation of 2-acetamido-2-deoxy sugars situated at the reducing end of oligosaccharides.3Specific cleavage of the glycosidic bond between the oligosaccharide and ceramide portions in glycolipids.4Specific degradation of 4-substituted pentose residues at the reducing end of oligosaccharides.5N-Deacetylation of 2-acetamido-2-deoxy sugar units in oligo- and polysaccharides.
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