Enzyme electrochemical preparation of a 3-keto derivative of 1,5-anhydro-D-glucitol using glucose-3-dehydrogenase

Appl Biochem Biotechnol. 2000 Spring:84-86:947-54. doi: 10.1385/abab:84-86:1-9:947.

Abstract

A novel enzymatic organic synthesis was reported, utilizing glucose-3-dehydrogenase (G3DH) and its regeneration via electrochemical methods. We combined the water-soluble G3DH prepared from a marine bacterium, Halomonas sp. alpha-15, and electron mediator with the electrode system in order to regenerate the enzyme. Using this system, the conversion of 1,5-anhydro-D-glucitol (1,5AG), a diabetes marker in human blood, was investigated. The final yield of the product, 3-keto anhydroglucitol (3-ketoAG), which was identified by 13C nuclear magnetic resonance, was 82% based on the initial amount of 1,5AG. The electrochemical yield of the reaction proceeded almost stoichiometrically. The electrochemical conversion rate of 1,5AG was 1.24 mmol/(L.h), and the electrochemical yield of 1,5AG consumption was 80%, whereas that for 3-ketoAG was 60%.

MeSH terms

  • Biomarkers / blood
  • Deoxyglucose* / blood
  • Diabetes Mellitus / blood
  • Diabetes Mellitus / diagnosis
  • Electrochemistry / methods
  • Glucose 1-Dehydrogenase
  • Glucose Dehydrogenases* / isolation & purification
  • Glucose Dehydrogenases* / metabolism
  • Halomonas / enzymology
  • Humans
  • Molecular Structure
  • Seawater / microbiology
  • Sorbitol / analogs & derivatives
  • Sorbitol / chemical synthesis*
  • Sorbitol / chemistry

Substances

  • Biomarkers
  • Sorbitol
  • 1,5-anhydroglucitol
  • Deoxyglucose
  • Glucose Dehydrogenases
  • Glucose 1-Dehydrogenase