Novel oligosaccharides synthesized from sucrose donor and cellobiose acceptor by alternansucrase

Carbohydr Res. 2001 Apr 23;331(4):403-11. doi: 10.1016/s0008-6215(01)00038-6.

Abstract

Cellobiose was tested as acceptor in the reaction catalyzed by alternansucrase (EC 2.4.1.140) from Leuconostoc mesenteroides NRRL B-23192. The oligosaccharides synthesized were compared to those obtained with dextransucrase from L. mesenteroides NRRL B-512F. With alternansucrase and dextransucrase, overall oligosaccharide synthesis yield reached 30 and 14%, respectively, showing that alternansucrase is more efficient than dextransucrase for cellobiose glucosylation. Interestingly, alternansucrase produced a series of oligosaccharides from cellobiose. Their structure was determined by mass spectrometry and [13C-1H] NMR spectroscopy. Two trisaccharides are first produced: alpha-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->4)]-D-glucopyranose (compound A) and alpha-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->4)-D-glucopyranose (compound B). Then, compound B can in turn be glucosylated leading to the synthesis of a tetrasaccharide with an additional alpha-(1-->6) linkage at the non-reducing end (compound D). The presence of the alpha-(1-->3) linkage occurred only in the pentasaccharides (compounds C1 and C2) formed from tetrasaccharide D. Compounds B, C1, C2 and D were never described before. They were produced efficiently only by alternansucrase. Their presence emphasizes the difference existing in the acceptor reaction selectivity of the various glucansucrases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Cellobiose / metabolism*
  • Glucosyltransferases / metabolism
  • Glycoside Hydrolases / metabolism*
  • Glycosyltransferases*
  • Leuconostoc / enzymology
  • Molecular Sequence Data
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligosaccharides / biosynthesis*
  • Sucrose / metabolism*

Substances

  • Oligosaccharides
  • Cellobiose
  • Sucrose
  • Glycosyltransferases
  • Glucosyltransferases
  • alternansucrase
  • dextransucrase
  • Glycoside Hydrolases