Knirel YA, Naumenko OI, Senchenkova SN, Perepelov AV Chemical methods for selective cleavage of glycosidic linkages in structural analysis of bacterial polysaccharides Russian Chemical Reviews = Uspekhi Khimii88(4) (2019)
406-424
Publication DOI:10.1070/RCR4856 Journal NLM ID:0404506 Publisher: London: Chemical Society Correspondence: Yu.A. Knirel <yknirelgmail.com> Institutions: N.D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences
This review is devoted to methods for the selective cleavage of glycosidic bonds. The mechanisms of reactions underlying these methods are considered and examples of their practical application in the structural analysis of bacterial polysaccharides are given. Specific methods for the selective cleavage of polysaccharides, remaining relevant for researchers, include the Smith degradation based on destruction of monosaccharides containing vicinal diol groups, dephosphorylation of phosphate-containing polysaccharides with hydrofluoric acid and the hydrolytic cleavage of glycosyl phosphate bonds in the latter compounds. Non-specific methods, including partial acid hydrolysis, acetolysis and solvolysis with anhydrous organic (CF3SO3H, MeSO3H, CF3CO2H) and inorganic (HF) acids do not make any specific demands on the composition and structure of the polysaccharide and are sensitive to its fine structural features. The review addesses the issue of stability of glycosidic bonds in various monosaccharides to reagents used for non-specific selective cleavage.
structural analysis, Bacterial polysaccharide, selective cleavage, glycosidic bond
Methods: partial acid hydrolysis, HF solvolysis, acid hydrolysis, mild acid hydrolysis, alkaline degradation, b-elimination, Smith degradation, deamination, de-O-acetylation, HF treatment, reduction with NaBD4, triflic acid solvolysis, acetolysis, Li/ethylenediamine degradation, hydrazinolysis, reduction with NaBH4, mild acid degradation, trifluoroacetic acid solvolysis, partial solvolysis with trifluoroacetic acid, de-N-acetylation with hydrazine, part acid hydrolysis, HF solvolysis; published polymerization frame was shifted for conformity with other records. Comments, role: review; oligosaccharide was obtained by selective cleavage of CPS (53) [0.1 M CF3CO2H, 100°C].
Related record ID(s): 1419, 1420 NCBI Taxonomy refs (TaxIDs):562 Reference(s) to other database(s): GTC:G99841JJ Show glycosyltransferases
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