Production of d-aldotetrose from l-erythrulose using various isomerases

Biosci Biotechnol Biochem. 2023 Jul 24;87(8):850-856. doi: 10.1093/bbb/zbad058.

Abstract

d-Aldotetroses are rare sugars that are obtained via chemical synthesis in low yield. In this study, we demonstrated that d-aldotetroses could be produced using 3 isomerases. First, l-erythrulose was epimerized using d-tagatose 3-epimerase from Pseudomonas cichorii ST-24. The specific optical rotation of the reaction solution gradually decreased to zero, indicating that approximately 50% of the l-erythrulose was converted to d-erythrulose. d, l-Erythrulose mixture was isomerized with d-arabinose isomerase from Klebsiella pneumoniae 40bXX to produce d-threose, resulting in a conversion rate of 9.35%. d-Erythrose production using l-rhamnose isomerase from Pseudomonas stutzeri LL172 resulted in a conversion rate of 12.9%. Because of the low purity of the purchased d-erythrose, the product was reduced by the Raney nickel catalyst compared with authentic erythritol. We confirmed the products using HPLC and 13C-NMR spectra. This is the first report of d-aldotetrose production using an enzymatic reaction.

Keywords: d-arabinose isomerase; d-erythrose; d-tagatose 3-epimerase; d-threose; l-rhamnose isomerase.

MeSH terms

  • Aldose-Ketose Isomerases*
  • Hexoses
  • Isomerases
  • Racemases and Epimerases
  • Tetroses*

Substances

  • erythrulose
  • Tetroses
  • Hexoses
  • Isomerases
  • Aldose-Ketose Isomerases
  • Racemases and Epimerases