Efficient one-pot enzymatic synthesis of alpha-(1-->4)-glucosidic disaccharides through a coupled reaction catalysed by Lactobacillus acidophilus NCFM maltose phosphorylase

Hiroyuki Nakai, Adiphol Dilokpimol, Maher Abou Hachem, Birte Svensson

Research output: Contribution to journalArticleScientificpeer-review

Abstract

Lactobacillus acidophilus NCFM maltose phosphorylase (LaMalP) of glycoside hydrolase family 65 catalysed enzymatic synthesis of alpha-(1-->4)-glucosidic disaccharides from maltose and five monosaccharides in a coupled phosphorolysis/reverse phosphorolysis one-pot reaction. Thus phosphorolysis of maltose to beta-glucose 1-phosphate circumvented addition of costly beta-glucose 1-phosphate for reverse phosphorolysis with different monosaccharide acceptors, resulting in 91%, 89%, 88%, 86% and 84% yield of alpha-d-glucopyranosyl-(1-->4)-N-acetyl-D-glucosaminopyranose [N-acetyl-maltosamine], alpha-D-glucopyranosyl-(1-->4)-D-glucosaminopyranose [maltosamine], alpha-D-glucopyranosyl-(1-->4)-D-mannopyranose, alpha-D-glucopyranosyl-(1-->4)-L-fucopyranose and alpha-D-glucopyranosyl-(1-->4)-D-xylopyranose, respectively, from 0.1M maltose, 0.5M N-acetyl glucosamine, 0.1M glucosamine, 0.1M mannose, 1M L-fucose and 0.5M xylose in 0.2M phosphate-citrate pH 6.2. These current yields of 0.27-0.34 g of disaccharide products from 10 mL reaction mixtures are easy to scale up and moreover the strategy can be applied to large-scale production of other oligosaccharides from low-cost disaccharides as catalysed by phosphorylases with different substrate specificities.

Original languageEnglish
Pages (from-to)1061-4
Number of pages4
JournalCarbohydrate Research
Volume345
Issue number8
DOIs
Publication statusPublished - 27 May 2010
MoE publication typeA1 Journal article-refereed

Keywords

  • Glycoside hydrolase family 65
  • Phosphorolysis
  • Reverse phosphorolysis
  • β-Glucose 1-phosphate
  • α-(1→4)-Glucosidic disaccharides

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