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Hydrolase-catalyzed beta-mannosylations

N Taubken1, J Thiem

  • 1Institut für Organische Chemie, Universität Hamburg, Germany.

Glycoconjugate Journal
|December 31, 1998
PubMed
Summary
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Enzymes beta-mannosidase and beta-galactosidase catalyze transmannosylation reactions, yielding beta1-4-linked disaccharides with hydrophobic acceptors. Enzyme activity and immobilization conditions were optimized for glycosidase applications.

Area of Science:

  • Biochemistry
  • Enzymology
  • Carbohydrate Chemistry

Background:

  • Glycosidases are crucial enzymes in carbohydrate metabolism and synthesis.
  • Transglycosylation reactions offer a pathway for synthesizing complex oligosaccharides.
  • Snail viscera beta-mannosidase and Aspergillus oryzae beta-galactosidase are potential biocatalysts for glycosidic bond formation.

Purpose of the Study:

  • To investigate transmannosylation reactions catalyzed by snail beta-mannosidase and Aspergillus beta-galactosidase.
  • To explore the synthesis of beta1-4-linked disaccharides using specific donor and acceptor substrates.
  • To determine optimal conditions for enzyme activity and immobilization for potential industrial applications.

Main Methods:

  • Transmannosylation reactions were performed using 4-nitrophenyl beta-D-mannopyranoside as the donor substrate.

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  • Hydrophobic acceptor molecules were employed to preferentially form beta1-4-linked disaccharides.
  • Enzyme activities in buffer-cosolvent mixtures were measured.
  • Immobilization conditions for both glycosidases were optimized.

    • Main Results:

    • Both beta-mannosidase and beta-galactosidase successfully catalyzed transmannosylation reactions.
    • The use of hydrophobic acceptors led to the preferential formation of beta1-4-linked disaccharides.
    • Enzyme activities were characterized in various buffer-cosolvent mixtures.
    • Optimized immobilization conditions were established for both enzymes.

    Conclusions:

    • Beta-mannosidase and beta-galactosidase are effective biocatalysts for synthesizing beta1-4-linked disaccharides via transmannosylation.
    • The choice of acceptor molecule significantly influences the regioselectivity of the glycosidic bond formation.
    • Optimized enzyme immobilization provides a basis for the efficient and potentially scalable application of these glycosidases in synthesis.