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Reactive thioglucoside substrates for β-glucosidase.

Elizabeth Alverson-Banks Avegno1, Scott J Hasty, Archana R Parameswar

  • 1Department of Chemistry, Tulane University, New Orleans, LA 70118, United States.

Archives of Biochemistry and Biophysics
|July 2, 2013
PubMed
Summary

New thioglycoside substrates, GlcSBiz and GlcSBox, are highly efficient for β-glucosidase enzymes from sweet almond and Aspergillus niger. These substrates exhibit unique hydrolysis mechanisms involving remote site protonation and thioglucosidic bond cleavage.

Keywords:
2-Mercaptobenzimidazoyl β-thioglucopyranosideRetentionSolvent kinetic isotope effectβ-Glucosidase

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Area of Science:

  • Biochemistry
  • Enzymology
  • Glycoscience

Background:

  • Thioglycosides are generally resistant to hydrolysis by acids and glycohydrolases.
  • β-glucosidases are crucial enzymes involved in carbohydrate metabolism.
  • Understanding enzyme-substrate interactions is key to developing novel biocatalysts.

Purpose of the Study:

  • To identify and characterize novel, efficient thioglycoside substrates for β-glucosidase.
  • To elucidate the mechanism of hydrolysis for these new substrates.
  • To compare the substrate efficiency and reaction mechanism with existing substrates.

Main Methods:

  • Synthesis of β-D-glucopyranosides of 2-mercaptobenzimidazole (GlcSBiz) and 2-mercaptobenzoxazole (GlcSBox).
  • Enzymatic hydrolysis assays using β-glucosidase from sweet almond (Family 1) and Aspergillus niger (Family 3).
  • Kinetic studies including solvent deuterium kinetic isotope effect (SKIE) measurements at varying pL.

Main Results:

  • GlcSBiz and GlcSBox were found to be excellent substrates for both sweet almond and Aspergillus niger β-glucosidases, with high catalytic efficiency comparable to p-nitrophenyl β-D-glucoside.
  • Enzyme-catalyzed hydrolysis of GlcSBiz proceeds with retention of configuration.
  • A modest solvent deuterium kinetic isotope effect on kcat was observed for GlcSBiz hydrolysis, suggesting a mechanism involving remote site protonation and subsequent thioglucosidic bond cleavage.

Conclusions:

  • The β-D-glucopyranosides of 2-mercaptobenzimidazole and 2-mercaptobenzoxazole represent a new class of highly efficient β-glucosidase substrates.
  • The hydrolysis mechanism involves protonation at the ring nitrogen followed by cleavage of the thioglucosidic bond, leading to a thione product.
  • These findings offer insights into the catalytic mechanisms of β-glucosidases and potential applications in glycoscience.