Synthesis using glycosidases

Bucke C (1996) Oligosaccharide synthesis using glycosidases. J Chem Technol Biotechnol... 

Successful examples were demonstrated for transesterilication, perhydrolysis and ammonolysis (using lipases, esterases, and proteases), amide/peptide synthesis (using proteases), epoxide hydrolysis (using epoxide hydrolases), and glycoside synthesis (using glycosidases). Even redox-transformations, such as carbonyl reduction and sulfoxidation were possible [113-119]. 

The resulting derivatives (269) can be considered as strategically important intermediates in the synthesis of glycosidase inhibitors and carbocyclic nucleosides (150). A new approach to the stereoselective synthesis of the piperidine ring with the use of [4+ 2] [3+ 2]-cycloaddition from specially prepared substrates is also very interesting (431)b, c. In the context of this problem, the conditions for the formation of systems containing quaternary vicinal stereocenters were found. 

Scheme 10.6 General strategy for the liquid-phase synthesis of disaccharides using glycosidases.

Synthesis and Modification of Carbohydrates Using Glycosidases and Lipases... 

As the chemical synthesis of glycosides is cumbersome, biotechnological transglycosidation using glycosidases is attracting more and more attention [60]. 

Fernandez-Mayoralas A (1997) Synthesis and Modification of Carbohydrates using Glycosidases and Lipases. 186 1-20... 

Table 17.3-7. Synthesis of oligosaccharides and other glycosides using glycosidases.

In addition to the freeze-concentration effect, a catalytic role for ice crystals, a favorable orientation of substrate and biocatalyst, the markedly lower dielectric constant of ice compared with water, and the high proton mobility in ice, have been discussed as further factors that possibly influence reactions in frozen systems. In summary, the reverse action of hydrolases provides an attractive alternative to the chemical synthesis of peptides but this approach could also be verified for the synthesis of oligosaccharides and oligonucleotides using glycosidases and ribonu-cleases, respectively11631. 

Fujimoto, H., Isomura, M., and Ajisaka, K. 1996. Synthesis of oligosaccharide components of glycoconjugates using glycosidases. J. Appl. Glycosci. 43 265-272. 

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